(3aR,6aS)-4-benzoyl-6-oxo-hexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(3aR,6aS)-4-benzoyl-6-oxo-hexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester
CAS No.:648936-08-7
Molecular Formula:C₂₁H₂₀N₂O₄
Molecular Weight:364.401
Hs Code.:

Synonyms:(3aR,6aS)-4-benzoyl-6-oxo-hexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

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Chemical Property of (3aR,6aS)-4-benzoyl-6-oxo-hexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

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Technology Process of (3aR,6aS)-4-benzoyl-6-oxo-hexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

There total 13 articles about (3aR,6aS)-4-benzoyl-6-oxo-hexahydropyrrolo[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: 78.0%

: 648936-07-6
(3aR,6S,6aS)-4-benzoyl-6-hydroxyhexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

: 648936-08-7
(3aR,6aS)-4-benzoyl-6-oxo-hexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: With Dess-Martin periodane; In dichloromethane; for 16h;
DOI:10.1016/j.bmc.2004.10.060

Reference yield:

: 648930-84-1
(-)-(R)-2-(2-hydroxyethyl)-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

: 648936-08-7
(3aR,6aS)-4-benzoyl-6-oxo-hexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 3.42 g / triethylamine / CH₂Cl₂ / 1 h / 0 °C

2.1: sodium azide / dimethylformamide / 1.5 h / 60 °C

3.1: triphenylphosphine / tetrahydrofuran / 7.5 h / 45 °C

4.1: sodium carbonate / dioxane; H₂O / 1 h

5.1: meta-chloroperbenzoic acid / CH₂Cl₂ / 16 h / 20 °C

6.1: hydrogen / Pd/C / ethanol / 0 - 20 °C

6.2: 61 percent / sodium carbonate / dioxane; H₂O / 1 h

7.1: HCl / dioxane / 1.08 h / 20 °C

8.1: N-methylmorpholine / dimethylformamide / 1.75 h / 20 °C

9.1: 78 percent / Dess-Martin periodinane / CH₂Cl₂ / 16 h

With 4-methyl-morpholine; hydrogenchloride; sodium azide; hydrogen; sodium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Schotten-Baumann reaction / 6.2: Schotten-Baumann reaction;
DOI:10.1016/j.bmc.2004.10.060

Reference yield:

: 648936-21-4
(R)-2-(2-aminoethyl)-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

: 648936-08-7
(3aR,6aS)-4-benzoyl-6-oxo-hexahydropyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium carbonate / dioxane; H₂O / 1 h

2.1: meta-chloroperbenzoic acid / CH₂Cl₂ / 16 h / 20 °C

3.1: hydrogen / Pd/C / ethanol / 0 - 20 °C

3.2: 61 percent / sodium carbonate / dioxane; H₂O / 1 h

4.1: HCl / dioxane / 1.08 h / 20 °C

5.1: N-methylmorpholine / dimethylformamide / 1.75 h / 20 °C

6.1: 78 percent / Dess-Martin periodinane / CH₂Cl₂ / 16 h

With 4-methyl-morpholine; hydrogenchloride; hydrogen; sodium carbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Schotten-Baumann reaction / 3.2: Schotten-Baumann reaction;
DOI:10.1016/j.bmc.2004.10.060