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Name	(2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylic acid	EINECS	N/A
CAS No.	364750-80-1	Density	1.150
PSA	66.84000	LogP	1.65440
Solubility	N/A	Melting Point	N/A
Formula	C11H19 N O4	Boiling Point	343 ºC
Molecular Weight	229.276	Flash Point	161 ºC
Transport Information	N/A	Appearance	N/A
Safety		Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	(2S,4R)-1-(tert-Butoxycarbonyl)-4-methylpyrrolidine-2-carboxylic acid; (2S,4R)-4-Methyl-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) ester	Article Data	8

(2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylic acid Synthetic route

: 220047-75-6
tert-butyl (2S,4R)-2-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate

: 364750-80-1
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In water; acetonitrile at 20℃; for 15h;	100%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; NaH2PO4 buffer; sodium hypochlorite In water; acetonitrile at 45℃; for 24h; pH=6.6;	84%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; potassium bromide In acetone at 0℃; for 2h;

: C11H19NO4

: 364750-80-1
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
Stage #1: C11H19NO4 With trimethylaluminum; N,O-dimethylhydroxylamine*hydrochloride In tetrahydrofuran; toluene at -30 - 23℃; for 0.666667h; Inert atmosphere; Stage #2: With methanesulfonyl chloride; triethylamine In tetrahydrofuran at -78 - 23℃; for 1h; Inert atmosphere; Further stages;	44%

: 61-90-5
L-leucine

: 24424-99-5
di-tert-butyl dicarbonate

A: 364750-81-2
N-tert-Butyloxycarbonyl-(2S,4S)-4-methylproline

B: (2S)-2-(ter-butoxycarbonylamino)-4,4-dimethyl-4-butanolide

C: 364750-80-1
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
Multistep reaction;	A n/a B 12% C n/a

: 24424-99-5
di-tert-butyl dicarbonate

: 364750-80-1
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: aqueous Na2CO3 / tetrahydrofuran; dioxane / 18 h 2.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C 3.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling 4.1: 78 percent / TEA; DMAP / CH2Cl2 5.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 6.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C 7.1: Raney-Ni; hydrogen / methanol / Heating 8.1: TBAF / tetrahydrofuran 9.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C View Scheme

Yield

Multi-step reaction with 9 steps
1.1: aqueous Na2CO3 / tetrahydrofuran; dioxane / 18 h
2.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C
3.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling
4.1: 78 percent / TEA; DMAP / CH2Cl2
5.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C
6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
6.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C
7.1: Raney-Ni; hydrogen / methanol / Heating
8.1: TBAF / tetrahydrofuran
9.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme

Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: lithium borohydride / tetrahydrofuran / 20 °C
View Scheme

: 61478-26-0
tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate

: 364750-80-1
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 78 percent / TEA; DMAP / CH2Cl2 2.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 3.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C 4.1: Raney-Ni; hydrogen / methanol / Heating 5.1: TBAF / tetrahydrofuran 6.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme

Yield

Multi-step reaction with 6 steps
1.1: 78 percent / TEA; DMAP / CH2Cl2
2.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C
3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
3.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C
4.1: Raney-Ni; hydrogen / methanol / Heating
5.1: TBAF / tetrahydrofuran
6.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme

: 13726-69-7
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

: 364750-80-1
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C 2.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling 3.1: 78 percent / TEA; DMAP / CH2Cl2 4.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 5.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 5.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C 6.1: Raney-Ni; hydrogen / methanol / Heating 7.1: TBAF / tetrahydrofuran 8.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme

Yield

Multi-step reaction with 8 steps
1.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C
2.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling
3.1: 78 percent / TEA; DMAP / CH2Cl2
4.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C
5.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
5.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C
6.1: Raney-Ni; hydrogen / methanol / Heating
7.1: TBAF / tetrahydrofuran
8.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme

: 125653-58-9
(2S,4R)-2-(tert-butyldimethylsilanyloxymethyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

: 364750-80-1
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 2.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C 3.1: Raney-Ni; hydrogen / methanol / Heating 4.1: TBAF / tetrahydrofuran 5.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme

Yield

Multi-step reaction with 5 steps
1.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C
2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
2.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C
3.1: Raney-Ni; hydrogen / methanol / Heating
4.1: TBAF / tetrahydrofuran
5.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme

: (2S,4R)-4-Hydroxy-2-isobutoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 364750-80-1
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling 2.1: 78 percent / TEA; DMAP / CH2Cl2 3.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 4.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 4.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C 5.1: Raney-Ni; hydrogen / methanol / Heating 6.1: TBAF / tetrahydrofuran 7.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme

Yield

Multi-step reaction with 7 steps
1.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling
2.1: 78 percent / TEA; DMAP / CH2Cl2
3.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C
4.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
4.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C
5.1: Raney-Ni; hydrogen / methanol / Heating
6.1: TBAF / tetrahydrofuran
7.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6
View Scheme

: 51-35-4
4R-4-hydroxyproline

: 364750-80-1
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: aqueous Na2CO3 / tetrahydrofuran; dioxane / 18 h 2.1: NMM / 1,2-dimethoxy-ethane / 0.5 h / -20 °C 3.1: 11.96 g / NaBH4 / 1,2-dimethoxy-ethane; H2O / 0.33 h / Cooling 4.1: 78 percent / TEA; DMAP / CH2Cl2 5.1: 88 percent / trichloroisocyanuric acid; TEMPO / CH2Cl2 / 1 h / 0 °C 6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 6.2: 73 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C 7.1: Raney-Ni; hydrogen / methanol / Heating 8.1: TBAF / tetrahydrofuran 9.1: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme

Yield

: 181295-78-3
(S)-tert-butyl 2-(hydroxymethyl)-4-methylenepyrrolidine-1-carboxylate

: 364750-80-1
(2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / Ir(COD)PyPCy3PF6; hydrogen / CH2Cl2 / 18 h / 20 °C / 760 Torr 2: 84 percent / NaClO2; TEMPO; aqueous NaH2PO4 buffer / NaClO / H2O; acetonitrile / 24 h / 45 °C / pH 6.6 View Scheme

(2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylic acid Chemical Properties

Product Name: (2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylic acid
Molecular Structure of (2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylic acid (CAS NO.364750-80-1):

Molecular Formula: C₁₁H₁₉NO₄
Molecular Weight: 229.2729
Synonyms of (2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylic acid (CAS NO.364750-80-1): (2S,4R)-1-(tert-Butoxycarbonyl)-4-methylpyrrolidine-2-carboxylic acid ; (2S,4R)-4-Methyl-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) ester
CAS NO: 364750-80-1
Index of Refraction: 1.491
Molar Refractivity: 57.644 cm³
Molar Volume: 199.2 cm³
Surface Tension: 42.049 dyne/cm
Density: 1.151 g/cm³
Flash Point: 161.361 °C
Enthalpy of Vaporization: 64.509 kJ/mol
Boiling Point of (2S,4R)-N-Boc-4-methylpyrrolidine-2-carboxylic acid (CAS NO.364750-80-1): 343.199 °C at 760 mmHg

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