(2S,4R)-4-Benzyl-5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Base Information

• Chemical Name: (2S,4R)-4-Benzyl-5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester
• CAS No.: 750638-93-8
• Molecular Formula: C₁₉H₂₇NO₅
• Molecular Weight: 349.427
• Mol file: 750638-93-8.mol

Synonyms:(2S,4R)-4-Benzyl-5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Chemical Property of (2S,4R)-4-Benzyl-5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-4-Benzyl-5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

There total 1 articles about (2S,4R)-4-Benzyl-5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-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:

ethyl (2S,4R)-1-(tert-butoxycarbonyl)-4-benzylpyroglutamate (153080-85-4) → (2S,4R)-4-Benzyl-5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (750638-93-8)

Guidance literature:

With dihydrogen peroxide; lithium triethylborohydride; In tetrahydrofuran; 1.) -78 deg C, 30 min; 2.) 0 deg C, 20 min;

DOI:10.1021/jo00121a020

Reference yield:

methanol (67-56-1) + (2S,4R)-4-Benzyl-5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (750638-93-8) → (4R)-Nα-tert-butoxycarbonyl-4-benzyl-5-methoxy-L-proline ethyl ester (464173-85-1)

Guidance literature:

With toluene-4-sulfonic acid; Yield given; Ambient temperature;

DOI:10.1021/jo00121a020

Reference yield:

(2S,4R)-4-Benzyl-5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (750638-93-8) → (3S,6S,7R,9S)-ethyl 2-oxo-3-Nα-(benzyloxycarbonyl)amino-7-benzyl-1-azabicyclo[4.3.0]nonane-9-carboxylate

Guidance literature:

Multi-step reaction with 7 steps

1.1: 4900 mg / (p-CH₃C₆H₄)SO₃H*H₂O / 20 °C

2.1: 76 percent / BF₃*Et₂O / diethyl ether / 3 h / -78 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: 63 percent / (CH₃)2S / CH₂Cl₂ / 120 h / 20 °C

4.1: 100 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 4 h / 20 °C

5.1: 96 percent / H₂; Rh(I)(1,5-COD)(1,2-bis{(S,S)-2,5-di-Et-(c-C₄H₈P)}C₆H₄)OTf / methanol / 24 h / 3878.71 Torr

6.1: trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

7.1: 187 mg / (C₂H₅)3N / CH₂Cl₂ / 120 h / 20 °C

With (+)-1,2-bis-((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; boron trifluoride diethyl etherate; hydrogen; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane; 4.1: Horner-Emmons olefination;

DOI:10.1021/jo0203591

upstream raw materials:

ethyl (2S,4R)-1-(tert-butoxycarbonyl)-4-benzylpyroglutamate

Downstream raw materials:

(4R)-N^α-tert-butoxycarbonyl-4-benzyl-5-methoxy-L-proline ethyl ester

(4R,5S)-N^α-tert-butoxycarbonyl-5-[3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)allyl]-4-benzyl-L-proline ethyl ester

(4R,5S)-N^α-tert-butoxycarbonyl-4-benzyl-5-(2-oxoethyl)-L-proline ethyl ester

(4R,5S)-N^α-tert-butoxycarbonyl-5-allyl-4-benzyl-L-proline ethyl ester