(2S,3R)-N-tert-Butoxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3R)-N-tert-Butoxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic acid methyl ester
• CAS No.: 496841-07-7
• Molecular Formula: C18H23NO6
• Molecular Weight: 349.384
• Mol file: 496841-07-7.mol

Synonyms:(2S,3R)-N-methyl-N-(Z)-styryl-3-phenyloxirane-2-carboxamide;(2S,3R)-N-tert-butoxycarbonyl-3-benzyloxy-2-pyrrolidine carboxylic acid methyl ester;(+)-N-methyl-N-[(Z)-styryl]-3-phenyloxirane-2-carboxamide;(2S,3R)-N-tert-Butoxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic acid methyl ester;(2S,3R)-N-tert-butyloxycarbonyl-3-benzoyloxy-2-pyrrolidine carboxylic acid methyl ester;

Chemical Property of (2S,3R)-N-tert-Butoxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic acid methyl ester

Chemical Property:

• PSA: 82.14000
• Density: 1.22
• LogP: 2.33230

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,3R)-N-tert-Butoxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic acid methyl ester

There total 4 articles about (2S,3R)-N-tert-Butoxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic acid methyl 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:

di-tert-butyl dicarbonate (24424-99-5) → (2S,3R)-N-tert-Butyloxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic Acid Methyl Ester (496841-07-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

2: 90 percent / PPh₃; DEAD / tetrahydrofuran / 9 h / 0 - 20 °C

With triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 2: Mitsunobu reaction;

DOI:10.1021/jm070312d

Reference yield:

(2S,3S)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride (1844898-16-3) → (2S,3R)-N-tert-Butyloxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic Acid Methyl Ester (496841-07-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

2: 90 percent / PPh₃; DEAD / tetrahydrofuran / 9 h / 0 - 20 °C

With triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 2: Mitsunobu reaction;

DOI:10.1021/jm070312d

Reference yield:

trans-3-hydroxy-L-proline (4298-08-2) → (2S,3R)-N-tert-Butyloxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic Acid Methyl Ester (496841-07-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / HCl / 0 - 20 °C

2: 80 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

3: 90 percent / PPh₃; DEAD / tetrahydrofuran / 9 h / 0 - 20 °C

With hydrogenchloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 3: Mitsunobu reaction;

DOI:10.1021/jm070312d

upstream raw materials:

di-tert-butyl dicarbonate

trans-3-hydroxy-L-proline

(2S,3S)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride

Downstream raw materials:

(2S,3R)-3-hydroxy-2-pyrrolidinecarboxylic acid methyl ester trifluoroacetate

C₂₃H₃₄ClN₃O₂Si

(2R,3R)-3-(tert-butyldimethylsilanyloxy)-N-(3-chloro-4-cyano-2-methylphenyl)-2-((S)-1-hydroxy-2-methylpropyl)pyrrolidine-1-carboxamide

C₂₁H₂₇F₃ClN₃O₂Si