(3S,4S)-4-Allyl-5-oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester → [(1S,5S)-4-Oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester

Participants

Reaction Steps

(3S,4S)-4-Allyl-5-oxo-1-[(1R)-1-phenylethyl]-3-vinylpyrrolidine-3-carboxylic acid tert-butyl ester (130.0 mg, 0.37 mmol) was dissolved in benzene (8 mL). The second generation Grubbs' catalyst (31.0 mg, 0.04 mmol) was added, and the mixture was stirred at room temperature for two hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (15% ethyl acetate/hexane) to give 93.2 mg of the title compound as a yellow oil.

Provenance & Evidence