(2S,5S)-benzyl-5-cyano-1-methoxycarbonyl-2-pyrrolidinecarboxylate

Base Information

• Chemical Name: (2S,5S)-benzyl-5-cyano-1-methoxycarbonyl-2-pyrrolidinecarboxylate
• CAS No.: 146389-31-3
• Molecular Formula: C₁₅H₁₆N₂O₄
• Molecular Weight: 288.303
• Mol file: 146389-31-3.mol

Synonyms:(2S,5S)-benzyl-5-cyano-1-methoxycarbonyl-2-pyrrolidinecarboxylate

Chemical Property of (2S,5S)-benzyl-5-cyano-1-methoxycarbonyl-2-pyrrolidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-benzyl-5-cyano-1-methoxycarbonyl-2-pyrrolidinecarboxylate

There total 4 articles about (2S,5S)-benzyl-5-cyano-1-methoxycarbonyl-2-pyrrolidinecarboxylate 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: 66.0%

trimethylsilyl cyanide (7677-24-9) + (2S)-benzyl-5-methoxy-1-methoxycarbonyl-2-pyrrolidinecarboxylate (372187-39-8) → (2S,5S)-benzyl-5-cyano-1-methoxycarbonyl-2-pyrrolidinecarboxylate (146389-31-3) + (2S,5R)-benzyl-5-cyano-1-methoxycarbonyl-2-pyrrolidinecarboxylate (146356-03-8)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at -40 ℃; for 2h;

DOI:10.1016/0957-4166(96)00114-0

Reference yield:

N-methoxycarbonyl (S)-pyroglutamic acid benzylester (146356-00-5) → (2S,5S)-benzyl-5-cyano-1-methoxycarbonyl-2-pyrrolidinecarboxylate (146389-31-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / DIBAL-H / tetrahydrofuran; hexane / 0.25 h / -78 °C

2: 100 percent / p-TsOH / Ambient temperature

3: 27 percent / SnCl₄ / CH₂Cl₂ / 2 h / -40 °C

With tin(IV) chloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/0957-4166(96)00114-0

Reference yield:

(S)-5-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester (146356-01-6,146389-29-9) → (2S,5S)-benzyl-5-cyano-1-methoxycarbonyl-2-pyrrolidinecarboxylate (146389-31-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / p-TsOH / Ambient temperature

2: 27 percent / SnCl₄ / CH₂Cl₂ / 2 h / -40 °C

With tin(IV) chloride; toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1016/0957-4166(96)00114-0

upstream raw materials:

trimethylsilyl cyanide

(2S)-benzyl-5-methoxy-1-methoxycarbonyl-2-pyrrolidinecarboxylate

(S)-5-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester

N-methoxycarbonyl (S)-pyroglutamic acid benzylester

Downstream raw materials:

(2S,5S)-pyrrolidine-2,5-dicarboxylic acid