Benzyl chloroformate → benzyl(3aR,6aS)-6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate

HRID 1959429Notes

Reaction equation

HRID 1959429 reaction equation
C([N:8]1[CH2:12][C@@H:11]2[CH2:13][CH2:14][C:15](=[O:16])[C@@H:10]2[CH2:9]1)C1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>ClCCl>[O:16]=[C:15]1[C@@H:10]2[CH2:9][N:8]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:12][C@@H:11]2[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 25633329cis-2-Benzylhexahydrocyclopenta[c]pyrrol-4(1H)-one

Product 1

HCID 60006925benzyl(3aR,6aS)-6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylateYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3aR,6aS)-2-benzyl-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrol-6-one (19.8 g, 92 mmol) in dichloromethane (770 mL) was treated with benzyl chloroformate (26.7 g, 22.3 mL, 156 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure and the crude material obtained was purified using silica gel column chromatography using 40 to 99% EtOAc in hexanes to obtain benzyl(3aR,6aS)-6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate (11.2 g, 43.19 mmol, 47%) as a light yellow oil. NMR (400 MHz, CDCl3) δ 7.41-7.23 (m, 5H), 5.11 (d, J=4.2 Hz, 2H), 3.82-3.52 (m, 3H), 3.29-3.14 (m, J=5.6 Hz, 1H), 3.13-2.93 (m, J=11.1, 6.8 Hz, 1H), 2.81-2.68 (m, J=8.6, 3.6 Hz, 1H), 2.37 (t, J=7.8 Hz, 2H), 2.26-2.10 (m, 1H), 1.86 (s, 1H). LC/MS m/z 260.1 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude material obtained
  3. customwas purified

Sources & evidence

ORD record
ord-a2a793a4020f455c858274e0512bdb36
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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