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(R)-2-METHYL-CBS-OXAZABOROLIDINE
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Name

(R)-2-METHYL-CBS-OXAZABOROLIDINE

 EINECS -0
CAS No. 112022-83-0 Density 1.12 g/cm3
PSA 12.47000 LogP 3.48070
Solubility Not miscible or difficult to mix in water. Melting Point 85-95 ºC
Formula C18H20BNO Boiling Point 377.5 ºC at 760 mmHg
Molecular Weight 277.174 Flash Point 182.1ºC
Transport Information UN 1294 3/PG 2 Appearance white to light yellow crystal powder
Safety 36/37-62-33-29-16-2 Risk Codes 11-38-48/20-63-65-67-36/37-19
Molecular Structure Molecular Structure of 112022-83-0 ((R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole) Hazard Symbols FlammableF,HarmfulXn,IrritantXi
Synonyms

(3aR)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;1H,3H-Pyrrolo[1,2-c][1,3,2]oxazaborole,tetrahydro-1-methyl-3,3-diphenyl-, (R)-;(R)-Me-CBS;(R)-Me-Corey-Bakshi-Shibatareagent;(R)-Methyl-CBS;(R)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(R-Methyl-Corey-Bakshi-Shibata catalyst;

Article Data 8

(R)-2-METHYL-CBS-OXAZABOROLIDINE Synthetic route

22348-32-9, 63401-04-7, 112022-88-5, 112068-01-6

(S)-diphenylprolinol

13061-96-6

dihydroxy-methyl-borane

112022-83-0

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

Conditions
ConditionsYield
In hexane at 30℃; Solvent; Temperature; Inert atmosphere; Reflux;81%
823-96-1

Trimethylboroxine

22348-32-9

(R)-α,α-diphenylprolinol

112022-83-0

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

Conditions
ConditionsYield
In toluene Heating;
With borane In toluene at 20 - 150℃; for 4.5h;
In toluene at 20℃; for 0.5h;
13061-96-6

dihydroxy-methyl-borane

22348-32-9

(R)-α,α-diphenylprolinol

112022-83-0

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

Conditions
ConditionsYield
With 4 A molecular sieve In toluene at 20℃; for 1h;80 mg
In toluene Reflux; Dean-Stark;
7318-81-2

bis(methoxy)methylborane

22348-32-9

(R)-α,α-diphenylprolinol

A

67-56-1

methanol

B

112022-83-0

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

Conditions
ConditionsYield
In toluene at 20℃; for 1h; Product distribution / selectivity;
5447-74-5

methyl 3-(4-methoxybenzoyl)propionate

112022-83-0

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

848044-56-4

(S)-methyl 4-hydroxy-4-(4’-methoxyphenyl)butyrate

Conditions
ConditionsYield
With boron trifluoride-tetrahydrofuran complex In toluene at -78℃;96%

C51H60O7Si

112022-83-0

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

C51H62O7Si

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran; toluene at -40℃; for 2h;95%

methyl 2,4-bis(methoxymethoxy)-6-(3-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)-2-oxopropyl) benzoate

13292-87-0

dimethyl sulfide borane

112022-83-0

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

methyl 2,4-dihydroxy-6-(3-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)-2-oxopropyl) benzoate

Conditions
ConditionsYield
Stage #1: dimethyl sulfide borane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: methyl 2,4-bis(methoxymethoxy)-6-(3-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)-2-oxopropyl) benzoate In tetrahydrofuran at -20℃; for 12h; Reagent/catalyst;		90%
100331-89-3

8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one

112022-83-0

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

530084-79-8

8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one

Conditions
ConditionsYield
In tetrahydrofuran; hydrogenchloride; ethyl acetate liquid HCl;76%
357405-87-9

3-chloro-1-(3-isoxazolyl)-1-propanone

112022-83-0

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

357405-40-4

(S)-α-(2-Chloroethyl)-5-isoxazolemethanol

Conditions
ConditionsYield
With borane In tetrahydrofuran; methanol; toluene13%
77-78-1

dimethyl sulfate

112022-83-0

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

144119-12-0

(R)-(+)-1-methyl-α,α-diphenyl-2-pyrrolidinemethanol

Conditions
ConditionsYield
With potassium carbonate In water

(R)-2-METHYL-CBS-OXAZABOROLIDINE Chemical Properties

MF: C18H20BNO
MW: 277.17
Appearance: white to light yellow crystal powde
mp: 85-95 °C(lit.)
bp: 111 °C
density: 0.95 g/mL at 25 °C
refractive index: 68 ° (C=1, MeOH)
Fp: 40 °F
storage temp.: 2-8°C
Sensitive: Air & Moisture Sensitive

(R)-2-METHYL-CBS-OXAZABOROLIDINE Safety Profile

Hazard Codes: F,Xn,Xi
Risk Statements: 11-38-48/20-63-65-67-36/37-19
Safety Statements: 36/37-62-33-29-16-2
RIDADR: UN 1294 3/PG 2
F: 10
HazardClass: 3
PackingGroup: II
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