(2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl 2-methyl ester hydrochloride

Base Information

• Chemical Name: (2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl 2-methyl ester hydrochloride
• CAS No.: 144527-44-6
• Molecular Formula: C11H19NO5^.HCl
• Molecular Weight: 281.736
• Mol file: 144527-44-6.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, 4-hydroxy-, 1-(1,1-dimethylethyl) 2-methyl ester, hydrochloride,(2S-trans)- (9CI);1-tert-Butyl 2-Methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxy hydrochloride;O1-tert-butyl O2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate hydrochloride;

Chemical Property of (2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl 2-methyl ester hydrochloride

Chemical Property:

• PSA: 76.07000
• LogP: 1.26960

Purity/Quality:

99.3% ^*data from raw suppliers

(2S,4R)-BOC 4-HYDROXYPROLINE METHYL ESTER HCL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl 2-methyl ester hydrochloride

There total 2 articles about (2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl 2-methyl ester hydrochloride 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) + L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4R)-methyl-4-hydroxypyrrolidine-2-carboxylate hydrochloride (144527-44-6)

Guidance literature:

With triethylamine; In acetonitrile; at 0 - 20 ℃;

DOI:10.1002/anie.201302014

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → (2S,4R)-methyl-4-hydroxypyrrolidine-2-carboxylate hydrochloride (144527-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / methanol / 15 h / 0 - 20 °C

2: triethylamine / acetonitrile / 0 - 20 °C

With thionyl chloride; triethylamine; In methanol; acetonitrile;

DOI:10.1002/anie.201302014

Reference yield: 88.0%

(2S,4R)-methyl-4-hydroxypyrrolidine-2-carboxylate hydrochloride (144527-44-6) + p-toluenesulfonyl chloride (98-59-9) → (2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (88043-21-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 20h;

DOI:10.1002/anie.201302014

upstream raw materials:

4R-4-hydroxyproline

di-tert-butyl dicarbonate

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

(2S,4R)-1-benzyl-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid methyl ester

(2S,4R)-1-benzyl-4-hydroxyproline methyl ester

(2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Refernces