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

Participants

Reaction Steps

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.

Provenance & Evidence