(3S,3aS,6aR)-(3-hydroxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)phenylmethanone

Base Information

Chemical Name:(3S,3aS,6aR)-(3-hydroxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)phenylmethanone
CAS No.:648936-15-6
Molecular Formula:C₁₃H₁₆N₂O₂
Molecular Weight:232.282
Hs Code.:

Synonyms:(3S,3aS,6aR)-(3-hydroxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)phenylmethanone

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Chemical Property of (3S,3aS,6aR)-(3-hydroxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)phenylmethanone

Chemical Property:

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Technology Process of (3S,3aS,6aR)-(3-hydroxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)phenylmethanone

There total 13 articles about (3S,3aS,6aR)-(3-hydroxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)phenylmethanone 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:

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

: 648936-15-6
(3S,3aS,6aR)-(3-hydroxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)phenylmethanone

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethanol;
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

: 648936-15-6
(3S,3aS,6aR)-(3-hydroxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)phenylmethanone

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: hydrogen / Pd/C / ethanol

With 4-methyl-morpholine; hydrogenchloride; sodium azide; hydrogen; sodium carbonate; 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

: 648936-15-6
(3S,3aS,6aR)-(3-hydroxyhexahydropyrrolo[3,2-b]pyrrol-1-yl)phenylmethanone

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: hydrogen / Pd/C / ethanol

With 4-methyl-morpholine; hydrogenchloride; hydrogen; sodium carbonate; 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