ethyl (1R,3R,4S)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate → ethyl (1S,3R,4R)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate

Participants

Reaction Steps

To a solution of ethyl (1R, 3R, 4S)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate (791 mg, 2.91 mmol) obtained in Example 3 (a) in ethyl acetate (15 ml) was added 10% Pd—C (53 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 16 hours. After a filtration through Celite, the solvent was concentrated. The residue was purified by silica gel column chromatography (5% ethyl acetate/hexane), to give ethyl (1S, 3R, 4R)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate (601 mg, 76%).

Provenance & Evidence