(2S,5R)-5-allylpyrrolidine-1,2-dicarboxylic acid 1-benzylester 2-methylester

Base Information

• Chemical Name: (2S,5R)-5-allylpyrrolidine-1,2-dicarboxylic acid 1-benzylester 2-methylester
• CAS No.: 123457-52-3
• Molecular Formula: C₁₇H₂₁NO₄
• Molecular Weight: 303.358
• Mol file: 123457-52-3.mol

Synonyms:(2S,5R)-5-allylpyrrolidine-1,2-dicarboxylic acid 1-benzylester 2-methylester

Chemical Property of (2S,5R)-5-allylpyrrolidine-1,2-dicarboxylic acid 1-benzylester 2-methylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-5-allylpyrrolidine-1,2-dicarboxylic acid 1-benzylester 2-methylester

There total 7 articles about (2S,5R)-5-allylpyrrolidine-1,2-dicarboxylic acid 1-benzylester 2-methylester 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: 88.0%

5-allylpyrrolidine-2-carboxylic acid methyl ester + benzyl chloroformate (501-53-1,94274-21-2) → (2S,5R)-5-allylpyrrolidine-1,2-dicarboxylic acid 1-benzylester 2-methylester (123457-52-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jo801638u

Reference yield: 88.0%

benzyl chloroformate (501-53-1,94274-21-2) + (5R,2S)-5-allyl-pyrrolidine-2-carboxylic acid methyl ester (210345-08-7) → (2S,5R)-5-allylpyrrolidine-1,2-dicarboxylic acid 1-benzylester 2-methylester (123457-52-3)

Guidance literature:

With sodium hydride;

DOI:10.1039/c5ob00180c

Reference yield:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8) → (2S,5R)-5-allylpyrrolidine-1,2-dicarboxylic acid 1-benzylester 2-methylester (123457-52-3)

Guidance literature:

Multi-step reaction with 4 steps

1: L-Selectride / tetrahydrofuran / -78 °C

2: boron trifluoride diethyl etherate / -78 °C

3: trifluoroacetic acid / dichloromethane

4: sodium hydride

With boron trifluoride diethyl etherate; L-Selectride; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c5ob00180c

upstream raw materials:

benzyl chloroformate

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

methyl (S)-pyroglutamate

(2S)-5-allyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Downstream raw materials:

(2S,5R)-5-((E)-4-oxopent-2-enyl)pyrrolidine-1,2-dicarboxylic acid 1-benzylester 2-methylester

benzyl (2S,2αR,5R)-(+)-2-(1-hydroxybutyl)-5-[(E)-4-oxohept-2-enyl]pyrrolidine-1-carboxylate

benzyl (2S,2αR,5R)-(-)-5-allyl-2-(1-hydroxybutyl)pyrrolidine-1-carboxylate

benzyl (2S,2αS,5R)-(-)-5-allyl-2-(1-hydroxybutyl)pyrrolidine-1-carboxylate