(3aR,6aS)-2-oxohexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

Base Information

• Chemical Name: (3aR,6aS)-2-oxohexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester
• CAS No.: 214337-00-5
• Molecular Formula: C₁₉H₂₄N₂O₅
• Molecular Weight: 360.41
• Mol file: 214337-00-5.mol

Synonyms:(3aR,6aS)-2-oxohexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

Chemical Property of (3aR,6aS)-2-oxohexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,6aS)-2-oxohexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

There total 2 articles about (3aR,6aS)-2-oxohexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl 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: 71.0%

di-tert-butyl dicarbonate (24424-99-5) + (3aS,6aR)-5-oxohexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester (214336-99-9) → (3aR,6aS)-2-oxohexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (214337-00-5)

Guidance literature:

(3aS,6aR)-5-oxohexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -70 ℃; for 0.166667h;

di-tert-butyl dicarbonate; In tetrahydrofuran; at -75 ℃; for 2.5h; Further stages.;

DOI:10.1021/jm0102203

Reference yield:

trans-3-amino-2-ethoxycarbonylmethyl-pyrrolidine-1-carboxylic acid benzyl ester → (3aR,6aS)-2-oxohexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (214337-00-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: resolution via salt with (+)-di-p-toluyl-D-tartaric acid

2.1: 97 percent / tert-butylmagnesium chloride / tetrahydrofuran / 1.25 h / 0 - 20 °C

3.1: LHMDS / tetrahydrofuran / 0.17 h / -70 °C

3.2: 71 percent / tetrahydrofuran / 2.5 h / -75 °C

With tert-butylmagnesium chloride; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/jm0102203

Reference yield: 83.0%

(3aR,6aS)-2-oxohexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (214337-00-5) + methyl iodide (74-88-4) → (3S,3aR,6aS)-3-methyl-2-oxohexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (214337-01-6)

Guidance literature:

(3aR,6aS)-2-oxohexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -75 - -70 ℃; for 0.166667h;

methyl iodide; In tetrahydrofuran; at -75 - -70 ℃; for 0.75h; Further stages.;

DOI:10.1021/jm0102203

upstream raw materials:

di-tert-butyl dicarbonate

(3aS,6aR)-5-oxohexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Downstream raw materials:

(3S,3aR,6aS)-3-methyl-2-oxohexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester