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

Base Information

• Chemical Name: (2R,4R)-2-Benzyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
• CAS No.: 144527-39-9
• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.4
• Mol file: 144527-39-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (2R,4R)-2-Benzyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-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: 22.0%

(R)-2-Benzyl-4-((1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.02,6]dec-4-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (185026-91-9) → (2S,4R)-2-Benzyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester + (2R,4R)-2-Benzyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (144527-39-9)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; dichloromethane; Ambient temperature;

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → (2R,4R)-2-Benzyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (144527-39-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 54.5 g / imidazole / dimethylformamide / 20 °C

2.1: diisopropylamine; n-butyllithium; HMPA / tetrahydrofuran; hexane / -20 - 0 °C

2.2: tetrahydrofuran; hexane

3.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; tetrabutyl ammonium fluoride; diisopropylamine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jo048639z

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2R,4R)-2-Benzyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (144527-39-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaOH / dioxane / 2 h / 20 °C

2.1: benzene; methanol; hexane / 1 h / 20 °C

3.1: 54.5 g / imidazole / dimethylformamide / 20 °C

4.1: diisopropylamine; n-butyllithium; HMPA / tetrahydrofuran; hexane / -20 - 0 °C

4.2: tetrahydrofuran; hexane

5.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; n-butyllithium; tetrabutyl ammonium fluoride; diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo048639z

upstream raw materials:

(R)-2-Benzyl-4-((1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

di-tert-butyl dicarbonate

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Downstream raw materials:

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