(2S,3R)-1-Methyl-5-oxo-3-phenyl-pyrrolidine-2,2-dicarboxylic acid ethyl ester

Base Information

• Chemical Name: (2S,3R)-1-Methyl-5-oxo-3-phenyl-pyrrolidine-2,2-dicarboxylic acid ethyl ester
• CAS No.: 109838-78-0
• Molecular Formula: C₁₅H₁₇NO₅
• Molecular Weight: 291.304
• Mol file: 109838-78-0.mol

Synonyms:(2S,3R)-1-Methyl-5-oxo-3-phenyl-pyrrolidine-2,2-dicarboxylic acid ethyl ester

Chemical Property of (2S,3R)-1-Methyl-5-oxo-3-phenyl-pyrrolidine-2,2-dicarboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,3R)-1-Methyl-5-oxo-3-phenyl-pyrrolidine-2,2-dicarboxylic acid ethyl ester

There total 4 articles about (2S,3R)-1-Methyl-5-oxo-3-phenyl-pyrrolidine-2,2-dicarboxylic acid ethyl 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:

5,5-Diethoxycarbonyl-1-methyl-4-phenyl-pyrrolidin-2-one (109838-77-9) → (2S,3R)-1-Methyl-5-oxo-3-phenyl-pyrrolidine-2,2-dicarboxylic acid ethyl ester (109838-78-0)

Guidance literature:

With barium dihydroxide; In ethanol; at 70 ℃; for 0.333333h; Yield given;

DOI:10.1021/jo00228a037

Reference yield:

5,5-Diethoxycarbonyl-4-phenylpyrrolidin-2-one (13992-75-1) → (2S,3R)-1-Methyl-5-oxo-3-phenyl-pyrrolidine-2,2-dicarboxylic acid ethyl ester (109838-78-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, RT, 2.) DMF, RT, 1 h

2: aq. Ba(OH)2 / ethanol / 0.33 h / 70 °C

With barium dihydroxide; sodium hydride; In ethanol;

DOI:10.1021/jo00228a037

Reference yield:

2-acetylaminomalonic acid diethyl ester (1068-90-2) → (2S,3R)-1-Methyl-5-oxo-3-phenyl-pyrrolidine-2,2-dicarboxylic acid ethyl ester (109838-78-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) EtONa / 1.) EtOH, RT, 2.) EtOH, reflux, 24 h

2: 1.) NaH / 1.) DMF, RT, 2.) DMF, RT, 1 h

3: aq. Ba(OH)2 / ethanol / 0.33 h / 70 °C

With barium dihydroxide; sodium ethanolate; sodium hydride; In ethanol;

DOI:10.1021/jo00228a037

upstream raw materials:

5,5-Diethoxycarbonyl-1-methyl-4-phenyl-pyrrolidin-2-one

5,5-Diethoxycarbonyl-4-phenylpyrrolidin-2-one

ethyl cinnamate

2-acetylaminomalonic acid diethyl ester

Downstream raw materials:

(+/-)-clausenamide

(+/-)-(4R^*,5R^*,7R^*)-5-(α-hydroxybenzyl)-1-methyl-4-phenylpyrrolidin-2-one

(+/-)-(4R^*,5R^*,7S^*)-5-(α-hydroxybenzyl)-1-methyl-4-phenylpyrrolidin-2-one

(+/-)-(4R^*,5R^*)-5-benzoyl-1-methyl-4-phenylpyrrolidin-2-one