2549-14-6

Basic information

• Product Name: (R)-(+)-2-Phenylglycinol
• Synonyms: RARECHEM AL BW 2319;(R)-(-)-2-AMINO-1-PHENYLETHANOL;(R)-2-AMINO-1-PHENYLETHANOL;(R)-1-PHENYL-1-HYDROXY-2-AMINOETHANE;(R)-ALPHA-(AMINOMETHYL)BENZYL ALCOHOL;BENZENEMETHANOL, A-(AMINOMETHYL)-, (AR)-;(r)-(-)-à-(aminomethyl)benzyl alcohol;(r)-α-(aminomethyl)benzyl alcohol
• CAS NO: 2549-14-6
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• EINECS: 1308068-626-2
• Product Categories: pharmacetical;Benzene series;Amino Acid Derivatives
• Mol File: 2549-14-6.mol
• Article Data: 43

Chemical Properties

• Melting Point: 59-65 °C(lit.)
• Boiling Point: 160°C/17mm
• Flash Point: >230 °F
• Appearance: /
• Density: 1.104 g/cm³
• Vapor Pressure: 0.00148mmHg at 25°C
• Refractive Index: 1.572
• PKA: 12.04±0.35(Predicted)
• Sensitive: Air Sensitive
• BRN: 3196196
• CAS DataBase Reference: (R)-(+)-2-Phenylglycinol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-2-Phenylglycinol(2549-14-6)
• EPA Substance Registry System: (R)-(+)-2-Phenylglycinol(2549-14-6)

Safety Data

• Hazard Codes: C
• Statements: 22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3259 8/PG 3
• WGK Germany: 3
• F: 3-10-23-34
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 2549-14-6(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow powder

InChI:InChI=1/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2/t8-/m0/s1

Synthetic route

(R)-2-nitro-1-phenylethanol (145920-96-3) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol	100%

<2R-(2α(R*),3aα,4α,7α,7aα)>-β-<(Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)-oxy>-benzolethanamin → (R)-2-Amino-1-phenylethanol (2549-14-6) + <2S-(2α,3aα,4α,7α,7aα)>-2,3,3a,4,5,6,7,7a-Octahydro-2-methoxy-7,8,8-trimethyl-4,7-methanobenzofuran (81925-10-2)

Conditions	Yield
With hydrogenchloride In methanol	A 97% B 93.5%

(R)-2-azido-1-phenylethanol (134625-72-2) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal	95%
With lithium aluminium tetrahydride In diethyl ether for 3h; Heating;	90%
With hydrogen; sodium hydroxide In aq. phosphate buffer; water at 30℃; under 7500.75 Torr; for 4h; pH=9; Green chemistry;	87%
With hydrogen; Lindlar's catalyst In ethyl acetate at 25℃; under 2327.2 Torr; for 7h;
With palladium 10% on activated carbon; hydrogen In methanol

2-Aminoacetophenone (613-89-8) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With C30H29N2OP; iron(II) acetate In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;	94%
With Arthrobacter sp. TS-15 recombinant ephedrine dehydrogenase; NADH In aq. phosphate buffer at 25℃; pH=7.5; Kinetics; Green chemistry; Enzymatic reaction; enantioselective reaction;	n/a

(R)-Mandelonitrile (10020-96-9) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 3h; Ambient temperature;	92%
With lithium aluminium tetrahydride In diethyl ether
Multi-step reaction with 3 steps 1: 65 percent / pyridine / -20 °C 2: I2 / tetrahydrofuran 3: 88 percent / LiAlH4 / tetrahydrofuran / 4 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: N-methylimidazole / tetrahydrofuran / 3 h / 20 °C 2: 88 percent / LiAlH4 / tetrahydrofuran / 4 h / 0 °C View Scheme

(R)-(-)-2-benzylamino-1-(3-chlorophenyl)ethanol (185035-43-2) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
	92%

(R)-2-(2-hydroxy-2-phenylethyl)isoindoline-1,3-dione → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With hydrazine In water at 60℃;	89%

(R)-2-(diethylphosphoryloxy)-2-phenylacetonitrile (604808-44-8) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃;	88%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 4h;	88%

(2R)-mandelamide (4358-86-5, 4410-31-5, 24008-63-7, 24008-62-6) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;	84%
With LiAlH In tetrahydrofuran 1.) reflux, 8 h, 2.) r.t., overnight;	78%
With lithium aluminium tetrahydride

(E)-2-oxo-2-phenylacetaldehyde O-methyl oxime (75735-33-0) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With yeast Saccharomyces cerevisiae optical yield given as %ee;	77%

(R)-2-bromo-1-phenylethanol (73908-23-3) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With ammonia In water at 20℃; for 2h;	75%

dl-threo-phenylserine (69-96-5, 1078-17-7, 2584-74-9, 2584-75-0, 6254-48-4, 7352-06-9, 7687-36-7, 7695-56-9, 32946-42-2, 50897-27-3, 68296-26-4, 109120-55-0) + glycine (56-40-6) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
Stage #1: dl-threo-phenylserine; glycine With manganese(ll) chloride In phosphate buffer at 25℃; for 24h; pH=5.5; Stage #2: With Pseudomonas putida L-threonine aldolase In phosphate buffer for 100h; pH=5.5; Further stages.;	57%

(E)-2-oxo-2-phenylacetaldehyde O-methyl oxime (75735-33-0) → (R)-2-hydroxy-2-phenylacetaldehyde O-methyl oxime + C9H13NO2 (1287753-57-4) + (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
Stage #1: (E)-2-oxo-2-phenylacetaldehyde O-methyl oxime With borane-THF; C13H24BNO2 In tetrahydrofuran at 0 - 20℃; for 3.5h; Stage #2: With methanol at 20℃; for 24h;	A 31% B 13% C 3%
With borane-THF; C13H24BNO2 at 20℃; for 18h;

2-Aminoacetophenone (613-89-8) → C16H20N2O2 + (S)-2-Amino-1-phenyl-1-ethanol (56613-81-1) + (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide; isopropyl alcohol Electrochemical reaction;	A 9% B n/a C n/a

2-Amino-1-phenylethanol (7568-93-6) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With MANDELIC ACID

hydrogen cyanide (74-90-8) + benzaldehyde (100-52-7) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
(i) (enzymatic transformation), (ii) LiAlH4, Et2O; Multistep reaction;

benzoyl cyanide (613-90-1) → (S)-2-Amino-1-phenyl-1-ethanol (56613-81-1) + (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With sodium tetrahydroborate; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; cobalt(II) chloride 2.) methanol; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

(2R)-N-ethoxycarbonyl-2-phenyl-2-hydroxyethylamine (144372-49-6) → (S)-2-Amino-1-phenyl-1-ethanol (56613-81-1) + (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With potassium hydroxide In methanol; water for 40h; Heating; Yields of byproduct given. Title compound not separated from byproducts;

(R)-(2-hydroxy-2-phenyl-ethyl)carbamic acid tert-butyl ester (86013-50-5) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With trifluoroacetic acid In water at 25℃; for 0.5h; Yield given;

(R)-benzyl N-(2-hydroxy-2-phenylethyl)carbamate (144372-50-9) → (S)-2-Amino-1-phenyl-1-ethanol (56613-81-1) + (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With potassium hydroxide In methanol; water for 40h; Heating; Yields of byproduct given. Title compound not separated from byproducts;

(R)-(+)-α-<(tert-butyldimethylsilyl)oxy>-benzeneacetonitrile (120390-75-2) → (S)-2-Amino-1-phenyl-1-ethanol (56613-81-1) + (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

2-amino-1-phenylethanol hydrochloride (4561-43-7) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Butyric acid (R)-2-butyrylamino-1-phenyl-ethyl ester (144372-51-0) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With potassium hydroxide In methanol; water for 40h; Heating;	260 mg

Butyric acid (S)-2-ethoxycarbonylamino-1-phenyl-ethyl ester (144315-90-2) → (S)-2-Amino-1-phenyl-1-ethanol (56613-81-1) + (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With potassium hydroxide In methanol; water for 40h; Heating; Yields of byproduct given. Title compound not separated from byproducts;

Butyric acid (S)-2-benzyloxycarbonylamino-1-phenyl-ethyl ester (144315-91-3) → (S)-2-Amino-1-phenyl-1-ethanol (56613-81-1) + (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With potassium hydroxide In methanol; water for 40h; Heating; Yields of byproduct given. Title compound not separated from byproducts;

(R)-N-(2-hydroxy-2-phenylethyl)acetamide (149342-37-0) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With hydrogenchloride In methanol
With hydrogenchloride; water at 110℃; for 24h;	0.6 mg

(2S)-N-ethoxycarbonyl-2-phenyl-2-hydroxyethylamine → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With hydrogenchloride In methanol

Thiophene-2-carboxylic acid ((R)-2-hydroxy-2-phenyl-ethyl)-amide (149286-02-2) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With hydrogenchloride In methanol

(-)-N-benzoyl-2-hydroxy-2-phenylethylamine (111059-46-2) → (R)-2-Amino-1-phenylethanol (2549-14-6)

Conditions	Yield
With hydrogenchloride In methanol
With potassium hydroxide In ethanol; water at 80℃; for 8h; Substitution;

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-Amino-1-phenylethanol (2549-14-6) → (R)-(2-hydroxy-2-phenyl-ethyl)carbamic acid tert-butyl ester (86013-50-5)

Conditions	Yield
	100%
In tetrahydrofuran at 20℃;	100%
With triethylamine In dichloromethane at 20℃; for 3h;	99%
In tetrahydrofuran at 20℃; for 3h;	89.1%
In chloroform at 0℃; for 0.5h;

tert-butyl N-{2-[4-(isothiocyanatomethyl)benzamido]phenyl}carbamate (1448350-40-0) + (R)-2-Amino-1-phenylethanol (2549-14-6) → (R)-tert-butyl N-(2-(4-((3-(2-hydroxy-2-phenylethyl)thioureido)methyl)benzamido)phenyl)carbamate (1448350-47-7)

Conditions	Yield
In acetonitrile at 20℃; for 16h;	100%
In tetrahydrofuran at 20℃; for 18h;

(R)-2-Amino-1-phenylethanol (2549-14-6) + acrolein (107-02-8) → C22H26N2O2

Conditions	Yield
In chloroform at 20℃; for 0.166667h; Solvent;	100%

C44H48N4O4(2+)*2Cl(1-) + (R)-2-Amino-1-phenylethanol (2549-14-6) → C60H66N6O4(2+)*2Cl(1-)

Conditions	Yield
In dichloromethane at 20℃; for 20h; Inert atmosphere;	100%

2-(4-aminophenyl)ethyl chloride (81865-10-3) + (R)-2-Amino-1-phenylethanol (2549-14-6) → YM-208876 (391901-45-4)

Conditions	Yield
With triethylamine In methanol at 60 - 65℃; for 8h; Temperature;	97.6%

succinic acid anhydride (108-30-5) + (R)-2-Amino-1-phenylethanol (2549-14-6) → C12H15NO4 (1417721-52-8)

Conditions	Yield
In dichloromethane	97%
In dichloromethane	97%

1,4-dibromo-butane (110-52-1) + (R)-2-Amino-1-phenylethanol (2549-14-6) → (R)-(-)-1-phenyl-2-(pyrrolidin-1-yl)ethanol (87069-57-6)

Conditions	Yield
With sodium hydrogencarbonate In toluene at 105 - 118℃; Dean-Stark; Inert atmosphere;	97%

1-(ethoxycarbonylmethyl)benzimidazole (55175-50-3) + (R)-2-Amino-1-phenylethanol (2549-14-6) → (R)-N-(2-hydroxy-1-phenylethyl)-2-(1H-benzo[d]-imidazol-1-yl) acetamide

Conditions	Yield
In toluene at 180℃; for 0.166667h; Microwave irradiation;	96%

(R)-2-Amino-1-phenylethanol (2549-14-6) + 2-(2-aminothiazol-5-yl)-N-[4-(2-chloroethyl)phenyl]acetamide → mirabegron

Conditions	Yield
With triethylamine In methanol at 60 - 65℃; for 8h; Solvent;	96%

piperonal (120-57-0) + (R)-2-Amino-1-phenylethanol (2549-14-6) → (R)-E-β-((1, 3-benzodioxol-5-ylmethylene)amino)benzene-ethanol (179930-11-1)

Conditions	Yield
With toluene-4-sulfonic acid In toluene Reflux; Dean-Stark; Large scale;	95.4%

2-formylbenzene boronic acid (40138-16-7) + (R)-2-Amino-1-phenylethanol (2549-14-6) → (C6H4CHNCH2CH(C6H5)O)2B2O

Conditions	Yield
In chloroform byproducts: H2O; B compd. stirred with aminoalcohol in CHCl3 at room temp. for 10 min; solvent removed under reduced pressure;	95%
In chloroform for 0.166667h;	95%

(R)-2-Amino-1-phenylethanol (2549-14-6) + malonic acid dimethyl ester (108-59-8) → N,N'-bis[(R)-1-phenyl-2-hydroxyethyl]propane-1,3-diamide

Conditions	Yield
With lithium methanolate In n-heptane at 100℃; for 3h;	94%

(R)-2-Amino-1-phenylethanol (2549-14-6) + N-(4-fluoro-3-nitro-phenyl)-N-methyl-benzamide (658700-09-5) → N-[4-((R)-2-hydroxy-2-phenyl-ethylamino)-3-nitro-phenyl]-N-methyl-benzamide (863409-16-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 20 - 85℃; for 24h;	93.4%

(R)-2-Amino-1-phenylethanol (2549-14-6) + 1,1'-carbonyldiimidazole (530-62-1) → (5R)-5-phenyl-1,3-oxazolidin-2-one (54705-41-8)

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 16h;	92%

3-formyl-furan-2-ylboronic acid (27339-38-4) + (R)-2-Amino-1-phenylethanol (2549-14-6) → (OC4H2CHNCH2CH(C6H5)O)2B2O

Conditions	Yield
In chloroform byproducts: H2O; B compd. stirred with aminoalcohol in CHCl3 at room temp. for 10 min; solvent removed under reduced pressure;	92%
In chloroform for 0.166667h;	92%

N-(quinolin-8-yl)but‐3‐enamide + (R)-2-Amino-1-phenylethanol (2549-14-6) → 3-(((R)-2-hydroxy-2-phenylethyl)amino)-N-(quinolin-8-yl)butanamide

Conditions	Yield
With cesium acetate at 100℃; for 24h; Schlenk technique; chemoselective reaction;	92%

(R)-2-(2-(4-chlorobenzylamino)-2-oxoethyl)pent-4-enoic acid (1201482-21-4) + (R)-2-Amino-1-phenylethanol (2549-14-6) → C22H25ClN2O3 (1201482-32-7)

Conditions	Yield
Stage #1: (R)-2-(2-(4-chlorobenzylamino)-2-oxoethyl)pent-4-enoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: (R)-2-Amino-1-phenylethanol With dmap In N,N-dimethyl-formamide at 0 - 20℃;	91%

2,2'-bis-(bromomethyl)-1,1'-biphenyl (38274-14-5) + (R)-2-Amino-1-phenylethanol (2549-14-6) → (R)-2-(5H-dibenzo[c,e]azepin-6(7H)-yl)-1-phenylethanol

Conditions	Yield
With triethylamine In acetonitrile for 24h; Reflux;	91%

Burgess Reagent (29684-56-8) + (R)-2-Amino-1-phenylethanol (2549-14-6) → (S)-1,1-Dioxo-3-phenyl-1λ6-[1,2,5]thiadiazolidine-2-carboxylic acid methyl ester

Conditions	Yield
In tetrahydrofuran at 0 - 25℃; for 6h;	90%
at 0 - 25℃; for 6h;	90%

1,3-propanesultone (1120-71-4) + (R)-2-Amino-1-phenylethanol (2549-14-6) → 3-{[(2R)-2-hydroxy-2-phenylethyl]amino}-2-propanesulfonic acid

Conditions	Yield
In toluene; acetonitrile for 4h; Heating / reflux;	90%

3-(3,5-ditrifluoromethylphenylamino)-4-methoxybutane-3-en-1,2-dione (1223105-85-8) + (R)-2-Amino-1-phenylethanol (2549-14-6) → C20H14F6N2O3

Conditions	Yield
In methanol at 20℃; for 24h; Inert atmosphere;	90%

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-Amino-1-phenylethanol (2549-14-6) → [(R)-2-phenyl-propyl]-carbamic acid tert-butyl ester

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h;	89.1%

1-isoquinolinecarboxylic acid (486-73-7) + (R)-2-Amino-1-phenylethanol (2549-14-6) → (R)-(-)-N-(2-hydroxy-2-phenylethyl)isoquinoline-1-carboxamide

Conditions	Yield
Stage #1: 1-isoquinolinecarboxylic acid With triethylamine; methyl chloroformate In tetrahydrofuran at 20 - 22℃; for 2h; Stage #2: (R)-2-Amino-1-phenylethanol With triethylamine In tetrahydrofuran at 0 - 22℃;	89%
Stage #1: 1-isoquinolinecarboxylic acid With triethylamine; methyl chloroformate In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: (R)-2-Amino-1-phenylethanol With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	89%

Upstream product

• 4358-86-5 (2R)-mandelamide 
• 7568-93-6 2-Amino-1-phenylethanol 
• 613-90-1 benzoyl cyanide 
• 4561-43-7 2-amino-1-phenylethanol hydrochloride 
• 134625-72-2 (R)-2-azido-1-phenylethanol 
• 96-09-3 styrene oxide 
• 69-96-5 dl-threo-phenylserine 
• 56-40-6 glycine 
• 5468-37-1 2-aminoacetophenone hydrochloride 
• 4190-14-1 N-(2-oxo-2-phenylethyl)benzamide 
• 86087-13-0 4,6-dimethyl-2-phenyl-(2α,4α,6β)-1,3-dioxane 
• 1287753-48-3 (E)-2-oxo-2-phenylacetaldehyde O-benzyl oxime 
• 1287753-49-4 (E)-2-oxo-2-phenylacetaldehyde O-trityl oxime 
• 532-54-7 E-isonitrosoacetophenone 

Downstream Products

• 1236005-70-1 2-{[(Z)-(R)-2-Hydroxy-2-phenyl-ethylimino]-methyl}-phenol 
• 156317-12-3 (+)-(2R,2'R,2''R)-triphenylethan-2-olamine 
• 848410-00-4 4-(2-hydroxy-2-phenyl-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester 
• 1005791-53-6 ethyl (R)-2-{4-[2-((R)-2-hydroxy-2-phenylethylamino)ethyl]phenoxy}propanoate 
• 1005791-51-4 methyl (S)-2-{4-[2-((R)-2-hydroxy-2-phenylethylamino)ethyl]phenoxy}propanoate 
• 1192754-76-9 (R)-2-(diphenylphosphino)-N-(2-hydroxy-2-phenylethyl)-benzamide 
• 1192754-77-0 (R)-2-(2-(diphenylphosphino)benzamido)-1-phenylethyl 2-(diphenylphosphino)benzoate 
• 1218906-28-5 (2R,2'S,2S)-tris(2-phenylethan-2-ol)amine 
• 1234623-02-9 C₁₃H₁₃BrN₂O 
• 179930-11-1 (R)-E-β-((1, 3-benzodioxol-5-ylmethylene)amino)benzene-ethanol 
• 1092063-46-1 C₁₃H₁₅Br₂NO₂ 
• 34469-09-5 (R)-2-dimethylamino-1-phenyl-ethanol 
• 391901-45-4 YM-208876 
• 863409-16-9 N-[4-((R)-2-hydroxy-2-phenyl-ethylamino)-3-nitro-phenyl]-N-methyl-benzamide 

Relevant articles and documents

Method for synthesizing chiral alpha-amino alcohol compound

The invention discloses a method for synthesizing a chiral alpha-amino alcohol compound. The method comprises the following steps: sequentially adding an iron catalyst, a ligand, ketone, an organic solvent and silane into a reaction system at 20-30 DEG C in a nitrogen atmosphere, then stirring the obtained mixture, and carrying out column chromatography separation on the obtained product to obtain a product, namely chiral alpha-amino alcohol. According to the invention, the most high-yield iron catalyst in earth crust is used, and cheap silane (PMHS, 500 g/298 yuan) is adopted as a reducing agent, so the asymmetric reduction reaction of alpha-amino ketone can be efficiently achieved under mild conditions so as to obtain the high-yield optically-active chiral alpha-amino alcohol compound; and moreover, through the creative labor of the inventor, reaction yield can reach 99%, and meanwhile, the content of the target product in the generated reaction product is 99%.

Two enantiocomplementary ephedrine dehydrogenases from arthrobacter sp. TS-15 with broad substrate specificity

The recently identified pseudoephedrine and ephedrine dehydrogenases (PseDH and EDH, respectively) from Arthrobacter sp. TS-15 are NADH-dependent members of the oxidoreductase superfamily of short-chain dehydrogenases/reductases (SDRs). They are specific for the enantioselective oxidation of (+)-(S) N-(pseudo)ephedrine and (-)-(R) N-(pseudo)ephedrine, respectively. Anti-Prelog stereospecific PseDH and Prelog-specific EDH catalyze the regio- A nd enantiospecific reduction of 1-phenyl-1,2-propanedione to (S)-phenylacetylcarbinol and (R)-phenylacetylcarbinol with full conversion and enantiomeric excess of >99%. Moreover, they perform the reduction of a wide range of aryl-aliphatic carbonyl compounds, including ketoamines, ketoesters, and haloketones, to the corresponding enantiopure alcohols. The highest stability of PseDH and EDH was determined to be at a pH range of 6.0-8.0 and 7.5-8.5, respectively. PseDH was more stable than EDH at 25 °C with half-lives of 279 and 38 h, respectively. However, EDH is more stable at 40 °C with a 2-fold greater half-life than at 25 °C. The crystal structure of the PseDH-NAD+ complex, refined to a resolution of 1.83 ?, revealed a tetrameric structure, which was confirmed by solution studies. A model of the active site in complex with NAD+ and 1-phenyl-1,2-propanedione suggested key roles for S143 and W152 in recognition of the substrate and positioning for the reduction reaction. The wide substrate spectrum of these dehydrogenases, combined with their regio- A nd enantioselectivity, suggests a high potential for the industrial production of valuable chiral compounds.

Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via 2-Azaallyl Anion Benzylic Ring-Opening of Aziridines

The 1,3-diamine motif appears in numerous complex molecules, yet there are few methods for the stereoselective construction of this moiety. Herein, we demonstrate a stereocontrolled synthesis of 1,3-diamines, which bear up to three contiguous stereogenic centers, through benzylic ring-opening of aziridines with 2-azaallyl anion nucleophiles. Reactions proceed efficiently (yield up to 95%), diastereoselectively (dr up to >20:1), site selectively, and enantiospecifically to deliver products with differentiated amino groups.