7-Benzyl-2-oxo-7-azabicyclo[3.3.0]oct-3-ene → 2-Benzylhexahydrocyclopenta[c]pyrrol-4(1H)-one

HRID 1356559Notes

Reaction equation

HRID 1356559 reaction equation
[CH2:1]([N:8]1[CH2:15][CH:14]2[CH: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]>[Rh].C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:15][CH:14]2[CH: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 185091437-Benzyl-2-oxo-7-azabicyclo[3.3.0]oct-3-eneHCID 178418361HCID 178418361, compound

Product 1

HCID 134637692-Benzylhexahydrocyclopenta[c]pyrrol-4(1H)-oneYield 84.1%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To an ethyl acetate (50 ml) solution of 7-benzyl-2-oxo-7-azabicyclo[3.3.0]oct-3-ene (1.45 g, 6.78 mmol) was added 5% rhodium-on-alumina (700 mg), and the mixture was stirred vigorously 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 1.22 g (5.70 mmol, 84%) of the title compound as a colorless oily substance. The TLC and 1H-NMR data of the product were in agreement with those of the product of Reference Example 1.

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-63bba9e0853846f7bb1ec79b08d8e1d0
Source dataset
uspto-grants-2003_07
Patent number
US06586604B2

Reaction notes

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