1-tert-butyl 2-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: 1-tert-butyl 2-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylate
• CAS No.: 121148-00-3
• Molecular Formula: C11H20N2O4
• Molecular Weight: 244.291
• Hs Code.: 2933990090
• European Community (EC) Number: 828-192-9
• DSSTox Substance ID: DTXSID40426588
• Nikkaji Number: J1.766.653C
• Wikidata: Q72450920
• Mol file: 121148-00-3.mol

Synonyms:121148-00-3;N-Boc-trans-4-amino-L-proline methyl ester;1-tert-butyl 2-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylate;(2S,4R)-1-tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate;1-O-tert-butyl 2-O-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylate;(2S,4R)-4-AMINO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-METHYL ESTER;396729-84-3;Methyl (2S,4R)-1-(tert-butoxycarbonyl)-4-aminopyrrolidine-2-carboxylate;1-tert-butyl 2-methyl trans-4-aminopyrrolidine-1,2-dicarboxylate;MFCD01861782;trans-4-Amino-N-Boc-L-proline methyl ester;Methyl (2S,4R)-4-amino-1-Boc-pyrrolidine-2-carboxylate;trans-1-tert-Butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate;SCHEMBL670493;AMY4375;DTXSID40426588;CS-M1798;AKOS016843354;DS-11136;N-Boc-trans-4-amino-proline methyl ester;EN300-88034;n-tert-butoxycarbonyl-trans-4-amino-l-proline methyl ester;trans-4-amino-n-tert-butoxycarbonyl-l-proline methyl ester;1-(tert-Butyloxycarbonyl)-4beta-amino-L-proline methyl ester;trans-1-tert-Butyl2-methyl4-aminopyrrolidine-1,2-dicarboxylate;(2S,4R)-4-amino-1-t- butoxycarbonyl-2-methoxycarbonylpyrrolidine;(2S,4R)-4-amino-1-t-butoxycarbonyl-2-methoxycarbonylpyrrolidine;1-t-butyl 2-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylate;1-t-butyl 2-methyl(2s,4r)-4-aminopyrrolidine-1,2-dicarboxylate;1-tert-Butyl 2-methyl (2S,4R)-4-amino-1,2-pyrrolidinedicarboxylate;Methyl (2S,4R)-4-amino-1-tert-butoxycarbonylpyrrolidine-2-carboxylate;methyl(2s,4r)-4-amino-1-tert-butoxycarbonylpyrrolidine-2-carboxylate;1,2-PYRROLIDINEDICARBOXYLIC ACID, 4-AMINO-, 1-(1,1-DIMETHYLETHYL) 2-METHYL ESTER, (2S,4R)-

Chemical Property of 1-tert-butyl 2-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.49
• Boiling Point: 320.687 °C at 760 mmHg
• PKA: 9.05±0.40(Predicted)
• Flash Point: 147.746 °C
• PSA: 81.86000
• Density: 1.152 g/cm³
• LogP: 1.13430
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 244.14230712
• Heavy Atom Count: 17
• Complexity: 311

Purity/Quality:

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

n-Boc-trans-4-amino-L-proline methyl ester 97.0% ^*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(CC1C(=O)OC)N
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)N

Technology Process of 1-tert-butyl 2-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylate

There total 22 articles about 1-tert-butyl 2-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylate 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: 97.3%

1-tert-butyl 2-methyl (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate (121147-97-5) → 1-(1,1-dimethylethyl) 2-methyl (2S,4R)-4-amino-1,2-pyrrolidinedicarboxylate (121148-00-3,1018667-18-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 12h;

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → 1-(1,1-dimethylethyl) 2-methyl (2S,4R)-4-amino-1,2-pyrrolidinedicarboxylate (121148-00-3,1018667-18-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 53.4 g / triethylamine / CH₂Cl₂ / 4 h / 0 - 5 °C

2: 56.2 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 5 °C

3: 88.7 percent / dimethylsulfoxide / 90 °C

4: 98.4 percent / potassium carbonate / methanol / 1 h / 20 °C

5: 100 percent / triethylamine / CH₂Cl₂ / 4 h / 0 - 5 °C

6: 90.8 percent / sodium azide / dimethylsulfoxide / 90 °C

7: H₂ / 10 percent Pd/C / methanol / 3 h / 20 °C / 2280 Torr

With sodium azide; hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0968-0896(01)00397-2

Reference yield:

(2S,4R)-4-(9H-Fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester → 1-(1,1-dimethylethyl) 2-methyl (2S,4R)-4-amino-1,2-pyrrolidinedicarboxylate (121148-00-3,1018667-18-9)

Guidance literature:

With pyrrolidine; In acetonitrile; at 20 ℃; for 3h;

upstream raw materials:

1-tert-butyl 2-methyl (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

(2S,4S)-2-methyl N-Boc-4-((methylsulfonyl)oxy)pyrrolidine-2-carboxylate

di-tert-butyl dicarbonate

Downstream raw materials:

1-tert-butyl 2-methyl (2S,4R)-4-(((4-methylphenyl)sulfonyl)amino)-1,2-pyrrolidinedicarboxylate

(2S,4R)-4-aminopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester hydrochloride

5-[(2S,4R)-N-9-fluorenylmethoxycarbonyl-2-methoxycarbonyl-4-(3’-carbamidopropanoyl)aminopyrrolidineallyl]-5’-O-(4,4’-dimethoxytrityl)-3’-O-acetyl-2’-deoxyuridine

1-tert-butyl 2-methyl (2S,4R)-4-(trans-2-allyl-cyclohexyloxycarbonylamino)-pyrrolidine-1,2-dicarboxylate

Refernces

• 1、 -. "Aromatic heterocyclic derivative and application of derivative in drug". Paragraph 0483; 0484; 0485. . Retrieved 2017/04/28.
• 2、 -. "Aromatic heterocyclic derivatives and applications of aromatic heterocyclic derivatives in medicines". Paragraph 1399-1401. . Retrieved 2016/10/09.