Sodium Hydroxide → (1S,5R)-1-Amino-7-methylene-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octane

Participants

Reaction Conditions

Reaction Steps

A 65% solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene (0.539 ml, 1.79 mmol) was added to a solution of (1S,5S)-1-amino-7-methylene-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octane (115 mg, 0.449 mmol) in toluene (2.24 ml), and the mixture was stirred at room temperature for 30 minutes and at 80° C. for 30 minutes. A 5 mol/l sodium hydroxide solution (15.0 ml) was added to the reaction solution with stirring under ice-cooling, followed by extraction with toluene (30 ml×1, 20 ml×1). The organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give 106 mg of the title compound.

Provenance & Evidence