benzyl (3aS,6S,6aR)-4-(cyclopropylcarbonyl)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1(2H)-carboxylate

Base Information

• Chemical Name: benzyl (3aS,6S,6aR)-4-(cyclopropylcarbonyl)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1(2H)-carboxylate
• CAS No.: 214337-02-7
• Molecular Formula: C₁₉H₂₂N₂O₄
• Molecular Weight: 342.395
• Mol file: 214337-02-7.mol

Synonyms:benzyl (3aS,6S,6aR)-4-(cyclopropylcarbonyl)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1(2H)-carboxylate

Chemical Property of benzyl (3aS,6S,6aR)-4-(cyclopropylcarbonyl)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1(2H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (3aS,6S,6aR)-4-(cyclopropylcarbonyl)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1(2H)-carboxylate

There total 3 articles about benzyl (3aS,6S,6aR)-4-(cyclopropylcarbonyl)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1(2H)-carboxylate 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: 35.0%

cyclopropanecarboxylic acid chloride (4023-34-1) + (3aS,6S,6aR)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester (214336-97-7) → benzyl (3aS,6S,6aR)-4-(cyclopropylcarbonyl)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1(2H)-carboxylate (214337-02-7)

Guidance literature:

(3aS,6S,6aR)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃; for 0.333333h;

cyclopropanecarboxylic acid chloride; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1021/jm030810w

Reference yield:

(3aS,6S,6aR)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester (214336-97-7) + cyclopropane carboxylic acid pivalic anhydride → benzyl (3aS,6S,6aR)-4-(cyclopropylcarbonyl)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1(2H)-carboxylate (214337-02-7)

Guidance literature:

(3aS,6S,6aR)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

cyclopropane carboxylic acid pivalic anhydride; In tetrahydrofuran; at -78 - 0 ℃; for 2h;

DOI:10.1016/S0960-894X(02)00294-9

Reference yield:

(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) → benzyl (3aS,6S,6aR)-4-(cyclopropylcarbonyl)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1(2H)-carboxylate (214337-02-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TFA / 1 h / 20 °C

2.1: LHMDS / tetrahydrofuran / 0.33 h / -78 - 0 °C

2.2: 35 percent / tetrahydrofuran / 1 h / -78 °C

With trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/jm030810w

upstream raw materials:

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

cyclopropanecarboxylic acid chloride

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