(2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2-oxoethyl)-pyrrolidine

Base Information

• Chemical Name: (2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2-oxoethyl)-pyrrolidine
• CAS No.: 936564-37-3
• Molecular Formula: C₁₆H₁₉NO₅
• Molecular Weight: 305.331
• Mol file: 936564-37-3.mol

Synonyms:(2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2-oxoethyl)-pyrrolidine

Chemical Property of (2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2-oxoethyl)-pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2-oxoethyl)-pyrrolidine

There total 5 articles about (2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2-oxoethyl)-pyrrolidine 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: 98.0%

(2R,5S)-1-benzyloxycarbonyl-2-methoxycarbonyl-5-(2-hydroxyethyl)pyrrolidine (1234804-82-0) → (2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2-oxoethyl)-pyrrolidine (936564-37-3)

Guidance literature:

(2R,5S)-1-benzyloxycarbonyl-2-methoxycarbonyl-5-(2-hydroxyethyl)pyrrolidine; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃;

With triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/j.tet.2010.04.037

Reference yield: 74.0%

(1R,5S)-N-benzyloxycarbonyl-2-methoxy-8-azabicyclo[3.2.1]oct-2-ene (936564-35-1) → (2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2-oxoethyl)-pyrrolidine (936564-37-3)

Guidance literature:

(1R,5S)-N-benzyloxycarbonyl-2-methoxy-8-azabicyclo[3.2.1]oct-2-ene; With ozone; In dichloromethane; at -78 ℃;

With triphenylphosphine; In dichloromethane; Further stages.;

DOI:10.1021/jo062532p

Reference yield:

(1R,5S)-N-benzyloxycarbonyl-2-oxo-8-azabicyclo[3.2.1]octane (936564-33-9) → (2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2-oxoethyl)-pyrrolidine (936564-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / p-toluenesulfonic acid monohydrate / 5 h / 80 °C

2.1: ozone / CH₂Cl₂ / -78 °C

2.2: 74 percent / triphenylphosphine / CH₂Cl₂

With toluene-4-sulfonic acid; ozone; In dichloromethane;

DOI:10.1021/jo062532p

upstream raw materials:

(1R,5S)-N-benzyloxycarbonyl-2-methoxy-8-azabicyclo[3.2.1]oct-2-ene

(1R,5S)-N-benzyloxycarbonyl-2-oxo-8-azabicyclo[3.2.1]octane

(5S)-8-methyl-8-azabicyclo[3.2.1]octan-2-one

benzyl chloroformate

Downstream raw materials:

(2R,5S)-N-benzyloxycarbonyl-2-methoxycarbonyl-5-(2,2-dimethoxyethyl)-pyrrolidine

(2R,5S,Z)-1-benzyloxycarbonyl2-methoxycarbonyl-5-(hex-2-enyl)-pyrrolidine

(2R,5S,Z)-1-benzyloxycarbonyl-2-methoxy-carbonyl-5-(pent-2-enyl)pyrrolidine