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

HRID 1934491Notes

Reaction equation

HRID 1934491 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-57c581a117324a1ebfed68a48417db15
Source dataset
uspto-grants-2002_05
Patent number
US06384050B1

Reaction notes

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