(3aR,5S,6S,6aR)-4-Benzyloxymethyl-6-bromo-5-hydroxy-hexahydro-cyclopenta[b]pyrrol-2-one

Base Information

Chemical Name:(3aR,5S,6S,6aR)-4-Benzyloxymethyl-6-bromo-5-hydroxy-hexahydro-cyclopenta[b]pyrrol-2-one
CAS No.:111803-50-0
Molecular Formula:C₁₅H₁₈BrNO₃
Molecular Weight:340.217
Hs Code.:

Synonyms:(3aR,5S,6S,6aR)-4-Benzyloxymethyl-6-bromo-5-hydroxy-hexahydro-cyclopenta[b]pyrrol-2-one

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Chemical Property of (3aR,5S,6S,6aR)-4-Benzyloxymethyl-6-bromo-5-hydroxy-hexahydro-cyclopenta[b]pyrrol-2-one

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Technology Process of (3aR,5S,6S,6aR)-4-Benzyloxymethyl-6-bromo-5-hydroxy-hexahydro-cyclopenta[b]pyrrol-2-one

There total 4 articles about (3aR,5S,6S,6aR)-4-Benzyloxymethyl-6-bromo-5-hydroxy-hexahydro-cyclopenta[b]pyrrol-2-one 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: 72.0%

: 111803-49-7
(3aR,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-1H-cyclopenta[b]pyrrol-2-one

: 111803-50-0
(3aR,5S,6S,6aR)-4-Benzyloxymethyl-6-bromo-5-hydroxy-hexahydro-cyclopenta[b]pyrrol-2-one

Guidance literature:: With N-Bromosuccinimide; water; In dimethyl sulfoxide; at 10 - 20 ℃; for 1h;
DOI:10.1139/v87-362

Reference yield:

: 111803-46-4,139562-50-8
(1S,4S)-5-Benzyloxymethyl-4-hydroxy-cyclopent-2-enecarboxylic acid methyl ester

: 111803-50-0
(3aR,5S,6S,6aR)-4-Benzyloxymethyl-6-bromo-5-hydroxy-hexahydro-cyclopenta[b]pyrrol-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 30 percent / 1.) NaH / diethyl ether / 1.) rt., 20 min 2.) -30 deg C then -25 deg C, 25 min

2: xylene / 6 h / 133 °C

3: 80 percent / NaBH₄ / ethanol / 0.5 h / 60 - 70 °C

4: 72 percent / N-bromosuccinimide, water / dimethylsulfoxide / 1 h / 10 - 20 °C

With sodium tetrahydroborate; N-Bromosuccinimide; water; sodium hydride; In diethyl ether; ethanol; dimethyl sulfoxide; xylene;
DOI:10.1139/v87-362

Reference yield:

: 111803-48-6
(1R,5S)-2-Benzyloxymethyl-5-(2,2,2-trichloro-acetylamino)-cyclopent-3-enecarboxylic acid methyl ester

: 111803-50-0
(3aR,5S,6S,6aR)-4-Benzyloxymethyl-6-bromo-5-hydroxy-hexahydro-cyclopenta[b]pyrrol-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / NaBH₄ / ethanol / 0.5 h / 60 - 70 °C

2: 72 percent / N-bromosuccinimide, water / dimethylsulfoxide / 1 h / 10 - 20 °C

With sodium tetrahydroborate; N-Bromosuccinimide; water; In ethanol; dimethyl sulfoxide;
DOI:10.1139/v87-362