(2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

Base Information

• Chemical Name: (2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester
• CAS No.: 865353-19-1
• Molecular Formula: C₂₃H₂₄N₂O₅
• Molecular Weight: 408.454
• Mol file: 865353-19-1.mol

Synonyms:(2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

Chemical Property of (2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester

There total 2 articles about (2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 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: 85.0%

(2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (865353-18-0) + benzyl bromide (100-39-0) → (2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester (865353-19-1)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/ja052377g

Reference yield:

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (13504-85-3) → (2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester (865353-19-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 1.5 h / 0 °C

1.2: 70 percent / tetrahydrofuran / 24 h / 20 °C

2.1: 85 percent / K₂CO₃ / dimethylformamide / 0 - 20 °C

With sodium hydride; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja052377g

Reference yield: 70.0%

(2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester (865353-19-1) + di-tert-butyl dicarbonate (24424-99-5) → (2S,4R)-4-(3-tert-Butoxycarbonylamino-propoxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester (865353-20-4)

Guidance literature:

With sodium tetrahydroborate; cobalt(II) chloride; In methanol; at 0 - 20 ℃;

DOI:10.1021/ja052377g

upstream raw materials:

(2S,4R)-4-(2-Cyano-ethoxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

benzyl bromide

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Downstream raw materials:

(2S,4R)-4-(3-tert-Butoxycarbonylamino-propoxy)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester