ethyl (2R,3S)-N-benzoxycarbonyl-3-hydroxypyrrolidine-2-carboxylate

Base Information

• Chemical Name: ethyl (2R,3S)-N-benzoxycarbonyl-3-hydroxypyrrolidine-2-carboxylate
• CAS No.: 131270-20-7
• Molecular Formula: C₁₅H₁₉NO₅
• Molecular Weight: 293.32
• Mol file: 131270-20-7.mol

Synonyms:ethyl (2R,3S)-N-benzoxycarbonyl-3-hydroxypyrrolidine-2-carboxylate

Chemical Property of ethyl (2R,3S)-N-benzoxycarbonyl-3-hydroxypyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2R,3S)-N-benzoxycarbonyl-3-hydroxypyrrolidine-2-carboxylate

There total 4 articles about ethyl (2R,3S)-N-benzoxycarbonyl-3-hydroxypyrrolidine-2-carboxylate 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%

3-oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester (51814-18-7) → ethyl (2R,3S)-N-benzoxycarbonyl-3-hydroxypyrrolidine-2-carboxylate (131270-20-7)

Guidance literature:

With Bakers yeast;

DOI:10.1016/S0040-4039(00)97933-4

Reference yield:

diethyl 2-azabutane-1,4-dicarboxylate (3783-61-7) → ethyl (2R,3S)-N-benzoxycarbonyl-3-hydroxypyrrolidine-2-carboxylate (131270-20-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / acetonitrile / 1 h / 0 °C

2: t-BuOK / toluene / 0.5 h / 0 °C

3: 45 percent / sucrose; baker's yeast / H₂O / 48 h / 40 °C

With baker's yeast; potassium tert-butylate; Sucrose; In water; toluene; acetonitrile; 1: Condensation / 2: Dickemann cyclization / 3: Reduction;

DOI:10.1139/v00-043

Reference yield:

ethyl N-benzoxycarbonyl-N-(2-ethoxcarbonylethyl)glycinate (51814-17-6) → ethyl (2R,3S)-N-benzoxycarbonyl-3-hydroxypyrrolidine-2-carboxylate (131270-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1: t-BuOK / toluene / 0.5 h / 0 °C

2: 45 percent / sucrose; baker's yeast / H₂O / 48 h / 40 °C

With baker's yeast; potassium tert-butylate; Sucrose; In water; toluene; 1: Dickemann cyclization / 2: Reduction;

DOI:10.1139/v00-043

upstream raw materials:

3-oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester

diethyl 2-azabutane-1,4-dicarboxylate

ethyl N-benzoxycarbonyl-N-(2-ethoxcarbonylethyl)glycinate

benzyl chloroformate

Downstream raw materials:

(1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizidine

(2R,3S,1'S,2'S)-N-benzoxycarbonyl-2-(1'-hydroxy-2'-thiophenyl-3'-butenyl)-3-methoxymethyloxypyrrolidine

(2R,3S,1'R)-N-benzoxycarbonyl-2-(1',4'-dihydroxy-2'butenyl)-3-methoxymethyloxypyrrolidine

(2R,3S)-N-benzoxycarbonyl-3-hydroxymethyl-3-methoxymethyloxypyrrolidine