tert-Butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate
• CAS No.: 330681-18-0
• Molecular Formula: C9H18N2O3
• Molecular Weight: 202.254
• Hs Code.: 2933998090
• European Community (EC) Number: 828-720-8
• Mol file: 330681-18-0.mol

Synonyms:tert-Butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate;190141-99-2;trans-3-Amino-1-Boc-4-hydroxypyrrolidine;3-Amino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester;MFCD14705159;(3R,4R)-3-Amino-1-Boc-4-hydroxypyrrolidine;1-Pyrrolidinecarboxylicacid,3-amino-4-hydroxy-,1,1-dimethylethylester(9CI);1-Boc-3-Aminopyrrolidin-4-ol;2-methyl-2-propanyl 3-amino-4-hydroxy-1-pyrrolidinecarboxylate;MFCD11111139;MFCD11111251;MFCD18072063;MFCD18072064;Tert-butyl 3-amino-4-hydroxy-pyrrolidine-1-carboxylate;(3R,4R)-1-Boc-3-amino-4-hydroxypyrrolidine;(3R,4S)-1-Boc-3-amino-4-hydroxypyrrolidine;SCHEMBL458822;CIS-(3S,4R)-TERT-BUTYL 3-AMINO-4-HYDROXYPYRROLIDINE-1-CARBOXYLATE;MOZOQDNRVPHFOO-UHFFFAOYSA-N;AKOS015920245;DS-1428;PB15864;PB19398;SB10500;SB11968;SB12525;AM803435;SY012550;SY023859;SY031135;SY033258;1-BOC-3-AMINO-4-HYDROXY-PYRROLIDINE;CS-0036146;FT-0682239;FT-0736721;FT-0771365;EN300-97295;(3S,4R)-1-Boc-3-amino-4-hydroxypyrrolidine;tert-Butyl3-amino-4-hydroxypyrrolidine-1-carboxylate;3-Amino-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester;t-butyl (3RS,4RS)-3-amino-4-hydroxypyrrolidine-1-carboxylate;tert-butyl(3S,4R)-3-amino-4-hydroxypyrrolidine-1-carboxylate;1-pyrrolidinecarboxylic acid,3-amino-4-hydroxy-,tert-butyl ester;tert. Butyl (3SR,4SR)-3-amino-4-hydroxy-pyrrolidine-1-carboxylate;1-Pyrrolidinecarboxylic acid, 3-amino-4-hydroxy-, 1,1-dimethylethyl ester;3-hydroxy-4-amino-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester;3-hydroxy4-amino-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester;1-PYRROLIDINECARBOXYLIC ACID, 3-AMINO-4-HYDROXY-, 1,1-DIMETHYLETHYL ESTER, (3R,4S)-REL-

Chemical Property of tert-Butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 308.8±42.0 °C(Predicted)
• PKA: 14.36±0.40(Predicted)
• PSA: 75.79000
• Density: 1.179
• LogP: 0.56350
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 202.13174244
• Heavy Atom Count: 14
• Complexity: 225

Purity/Quality:

98%,99%, ^*data from raw suppliers

tert-Butyl (3R,4R)-3-amino-4-hydroxypyrrolidine-1-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(C(C1)O)N

Technology Process of tert-Butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate

There total 6 articles about tert-Butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

(3R,4R)-3-azido-4-(trimethylsilanyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester (1202067-36-4) → (3R,4R)-3-amino-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (330681-18-0,138026-97-8,148214-90-8,190792-75-7)

Guidance literature:

(3R,4R)-3-azido-4-(trimethylsilanyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester; trifluoroacetic acid; In methanol; for 2h;

With hydrogen; platinum(IV) oxide; for 18h;

Reference yield:

N-(tert-butoxycarbonyl)-3-pyrroline (73286-70-1) → (3R,4R)-3-amino-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (330681-18-0,138026-97-8,148214-90-8,190792-75-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 18 h

2.1: (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino chromium(III) chloride / 4 h / 20 °C

3.1: trifluoroacetic acid / methanol / 2 h

3.2: 18 h

With 3-chloro-benzenecarboperoxoic acid; (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino chromium(III) chloride; trifluoroacetic acid; In methanol; dichloromethane;

Reference yield:

(3S,4R)-1-N-tert-butyloxycarbonyl-4-(4,4'-dimethoxytrityloxy)-3-mesyloxy-pyrrolidine (926912-99-4) → (3R,4R)-3-amino-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (330681-18-0,138026-97-8,148214-90-8,190792-75-7)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium azide / N,N-dimethyl-formamide / 100 °C

2: trifluoroacetic acid / dichloromethane / 0.5 h

3: palladium on activated charcoal; hydrogen / methanol

With sodium azide; palladium on activated charcoal; hydrogen; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm201409u

upstream raw materials:

(3R,4R)-3-azido-4-(trimethylsilanyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester

(3S,4R)-1-N-tert-butyloxycarbonyl-4-(4,4'-dimethoxytrityloxy)-3-mesyloxy-pyrrolidine

(3R,4R)-tert-butyl 3-azido-4-hydroxypyrrolidine-1-carboxylate

N-(tert-butoxycarbonyl)-3-pyrroline

Downstream raw materials:

3-[[2-amino-5-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-7-yl]amino]-4-hydroxy-(3R,4R)-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester

cis-3-amino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

(3R,4R)-tert-butyl 3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate

(3R,4R)-3-[4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoylamino]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 -. "THIENO-PYRIDINE DERIVATIVES AS MEK INHIBITORS". Page/Page column 43. . Retrieved 2010/01/12.