Benzyl chloroformate → 4-Oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid benzyl ester

HRID 1356552Notes

Reaction equation

HRID 1356552 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:19]1[CH2:26][CH:25]2[CH:21]([CH2:22][CH2:23][C:24]2=[O:27])[CH2:20]1)C1C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9]([N:19]1[CH2:26][CH:25]2[CH:21]([CH2:22][CH2:23][C:24]2=[O:27])[CH2:20]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformate2×HCID 134637692-Benzylhexahydrocyclopenta[c]pyrrol-4(1H)-one

Product 1

HCID 185091484-Oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid benzyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyloxycarbonyl chloride (5.14 ml, 36.0 mmol) was added dropwise to a solution of 7-benzyl-2-oxo-7-azabicyclo [3.3.0]octane (5.20 g, 24.2 mmol) in dichloromethane (50 ml) under cooling with ice, followed by stirring at room temperature for 24 hours. The mixture was again cooled with ice, and benzyloxycarbonyl chloride (5.14 ml, 36.0 mmol) was added thereto dropwise. After removing the solvent by evaporation, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 4.52 g (17.4 mmol, 72%) of the title compound as acolorless oily substance. 1H-NMR (400 MHz, CDCl3) δ: 1.80-1.90 (1H, m), 2.12-2.22 (1H, m), 2.35-2.39 (2H, m), 2.76 (1H, dt, J=3.5, 8.5 Hz), 3.01-3.11 (1H, m), 3.16-3.26 (1H, m), 3.61-3.66 (1H, m), 3.69-3.78 (1H, m), 5.11-5.12 (2H, m), 7.29-7.38 (5H, m)

Workup

  1. temperatureunder cooling with ice
  2. additionwas added
  3. customAfter removing the solvent
  4. customby evaporation
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-47bacc26ab00498cae97c0adfc3a978b
Source dataset
uspto-grants-2003_07
Patent number
US06586604B2

Reaction notes

Loading…