(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy)-6-piperidinylcarbonyl-1-phenyl-8-azabicyclo[3.2.1]octane → (1R*,2R*,5S*,6R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-6-piperidinylcarbonyl-1-phenyl-8-azabicyclo[3.2.1]octane

Participants

Reaction Steps

A mixture of (1R*,2R*,5S*,6R*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-piperidinylcarbonyl-1-phenyl-8-azabicyclo[3.2.1]octane (Example 120; 100 mg, 0.16 mmol), 10% palladium on charcoal (180 mg) and ethanol (10 ml) was stirred under hydrogen atmosphere (1 atm) at +65° C. for 1 hour. The reaction mixture was cooled to room temperature, flushed with nitrogen gas and filtered through a pad of Celite™. The filtrate was concentrated and purified chromatography on silica gel to give the title compound (83 mg, 90%). The hydrochloride salt of the title compound was prepared by treatment with ethereal HCl.

Provenance & Evidence