HCID 69847352, compound → cis-2-Benzylhexahydrocyclopenta[c]pyrrol-4(1H)-one

HRID 1934487Notes

Reaction equation

HRID 1934487 reaction equation
[CH2:1]([N:8]1[CH2:15][C@H:14]2[C@H:10]([CH:11]=[CH:12][C:13]2=[O:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.[Rh]>[CH2:1]([N:8]1[CH2:15][C@H:14]2[C@H:10]([CH2:11][CH2:12][C:13]2=[O:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 69847352HCID 69847352, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13463770cis-2-Benzylhexahydrocyclopenta[c]pyrrol-4(1H)-oneYield 83.1%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5% Rhodium-on-alumina (700 mg) was added to a solution of (1R,5S)-7-benzyl-2-oxo-7-azabicyclo[3.3.0]oct-3-ene (1.57 g, 7.34 mmol) in ethyl acetate (50 ml), and the mixture was vigorously stirred in a hydrogen atmosphere for 3.5 hours. The insoluble matter was removed by Celite filtration, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 1.31 g (6.10 mmol, 83%) of the title compound as a colorless oily substance.

Workup

  1. customThe insoluble matter was removed by Celite filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-91232b92dd934afd84c37c73d8ae2e81
Source dataset
uspto-grants-2002_05
Patent number
US06384050B1

Reaction notes

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