Acetic acid (3aR,5S,6S,6aR)-4-benzyloxymethyl-6-bromo-2-oxo-octahydro-cyclopenta[b]pyrrol-5-yl ester

Base Information

Chemical Name:Acetic acid (3aR,5S,6S,6aR)-4-benzyloxymethyl-6-bromo-2-oxo-octahydro-cyclopenta[b]pyrrol-5-yl ester
CAS No.:111803-51-1
Molecular Formula:C₁₇H₂₀BrNO₄
Molecular Weight:382.254
Hs Code.:

Synonyms:Acetic acid (3aR,5S,6S,6aR)-4-benzyloxymethyl-6-bromo-2-oxo-octahydro-cyclopenta[b]pyrrol-5-yl ester

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Chemical Property of Acetic acid (3aR,5S,6S,6aR)-4-benzyloxymethyl-6-bromo-2-oxo-octahydro-cyclopenta[b]pyrrol-5-yl ester

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Technology Process of Acetic acid (3aR,5S,6S,6aR)-4-benzyloxymethyl-6-bromo-2-oxo-octahydro-cyclopenta[b]pyrrol-5-yl ester

There total 5 articles about Acetic acid (3aR,5S,6S,6aR)-4-benzyloxymethyl-6-bromo-2-oxo-octahydro-cyclopenta[b]pyrrol-5-yl 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: 72.0%

: 108-24-7
acetic anhydride

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

: 111803-51-1
Acetic acid (3aR,5S,6S,6aR)-4-benzyloxymethyl-6-bromo-2-oxo-octahydro-cyclopenta[b]pyrrol-5-yl ester

Guidance literature:: With pyridine; for 2h; Ambient temperature;
DOI:10.1139/v87-362

Reference yield:

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

: 111803-51-1
Acetic acid (3aR,5S,6S,6aR)-4-benzyloxymethyl-6-bromo-2-oxo-octahydro-cyclopenta[b]pyrrol-5-yl ester

Guidance literature:: Multi-step reaction with 2 steps

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

2: 72 percent / pyridine / 2 h / Ambient temperature

With pyridine; N-Bromosuccinimide; water; In dimethyl sulfoxide;
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

: 111803-51-1
Acetic acid (3aR,5S,6S,6aR)-4-benzyloxymethyl-6-bromo-2-oxo-octahydro-cyclopenta[b]pyrrol-5-yl ester

Guidance literature:: Multi-step reaction with 5 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

5: 72 percent / pyridine / 2 h / Ambient temperature

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