(2R,4S)-4-(aMinoMethyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2R,4S)-4-(aMinoMethyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid
• CAS No.: 132622-86-7
• Molecular Formula: C11H20N2O4
• Molecular Weight: 244.2875
• Mol file: 132622-86-7.mol

Synonyms:(2R,4S)-4-(aMinoMethyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid;(2R-cis)-4-(Aminomethyl)-1,2-pyrrolidinedicarboxylic acid 1-(tert-butyl) ester

Chemical Property of (2R,4S)-4-(aMinoMethyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

Chemical Property:

• PSA: 92.86000
• Density: 1.197
• LogP: 1.29350

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,4S)-4-(aMinoMethyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

There total 4 articles about (2R,4S)-4-(aMinoMethyl)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 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: 95.0%

(2R,4R)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (132622-85-6) → (4R)-1-(tert-butoxycarbonyl)-4-(aminomethyl)-D-proline (132622-86-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; water; at 22 ℃; under 23271.7 Torr;

DOI:10.1021/jo00009a016

Reference yield:

(2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (77450-00-1) → (4R)-1-(tert-butoxycarbonyl)-4-(aminomethyl)-D-proline (132622-86-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / CBr₄, P(Ph₃) / CH₂Cl₂ / 16 h / 22 °C

2: 22 percent / n-Bu₄NCN / dimethylformamide / 20 h / 55 °C

3: 90 percent / 1M NaOH / methanol; H₂O / 22 °C

4: 95 percent / H₂ / 10percent Pd/C / H₂O; ethanol / 22 °C / 23271.7 Torr

With sodium hydroxide; carbon tetrabromide; hydrogen; tetra-n-butylammonium cyanide; triphenylphosphine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00009a016

Reference yield:

(4S)-1-(tert-butoxycarbonyl)-4-bromo-D-proline ethyl ester (132622-76-5) → (4R)-1-(tert-butoxycarbonyl)-4-(aminomethyl)-D-proline (132622-86-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 22 percent / n-Bu₄NCN / dimethylformamide / 20 h / 55 °C

2: 90 percent / 1M NaOH / methanol; H₂O / 22 °C

3: 95 percent / H₂ / 10percent Pd/C / H₂O; ethanol / 22 °C / 23271.7 Torr

With sodium hydroxide; hydrogen; tetra-n-butylammonium cyanide; palladium on activated charcoal; In methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00009a016

upstream raw materials:

(2R,4R)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

(2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester

(4S)-1-(tert-butoxycarbonyl)-4-bromo-D-proline ethyl ester

(4R)-1-(tert-butoxycarbonyl)-4-cyano-D-proline ethyl ester

Downstream raw materials:

(4R)-1-(tert-butoxycarbonyl)-4-<<<<(p-toluenesulfonyl)imino>aminomethyl>amino>methyl>-D-proline