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

Base Information

Chemical Name:(3aS,6S,6aR)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester
CAS No.:214336-97-7
Molecular Formula:C₁₅H₁₈N₂O₃
Molecular Weight:274.32
Hs Code.:

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

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

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

There total 2 articles about (3aS,6S,6aR)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl 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: 56.0%

: 214337-01-6
(3S,3aR,6aS)-3-methyl-2-oxohexahydropyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

: 214336-97-7
(3aS,6S,6aR)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: With trifluoroacetic acid; at 20 ℃; for 0.666667h;
DOI:10.1021/jm0102203

Reference yield:

: trans-3-amino-2-ethoxycarbonylmethyl-pyrrolidine-1-carboxylic acid benzyl ester

: 214336-97-7
(3aS,6S,6aR)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 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

4.1: LHMDS / tetrahydrofuran / 0.17 h / -75 - -70 °C

4.2: 83 percent / tetrahydrofuran / 0.75 h / -75 - -70 °C

5.1: 56 percent / trifluoroacetic acid / 0.67 h / 20 °C

With tert-butylmagnesium chloride; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran;
DOI:10.1021/jm0102203

Reference yield: 96.0%

: 214336-97-7
(3aS,6S,6aR)-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

: 214337-63-0
(c-2,c-3-dimethylcyclopropyl-r-1-carboxylic) anhydride

: 214337-06-1
benzyl (3aS,6S,6aR)-4-{[cis-2,3-dimethylcyclopropyl]-cis-carbonyl}-6-methyl-5-oxohexahydropyrrolo[3,2-b]pyrrole-1(2H)-carboxylate

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 ℃; for 0.333333h;

(c-2,c-3-dimethylcyclopropyl-r-1-carboxylic) anhydride; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1021/jm030810w