(1R*,2R*,4'S*,5R*)-8-Benzyl-4'-(2-benzyloxy-5-trifluoromethoxyphenyl)-6-(tert-butoxycarbonyl)-2',3',4',5'-tetrahydro-1-phenylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan] → (1R*,2R*,4'S*,5R*)-6-(tert-Butoxycarbonyl)-2',3',4',5'-tetrahydro-4'-(2-hydroxy-5-trifluoromethoxyphenyl)-1-phenylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

Participants

Reaction Steps

A mixture of (1R*,2R*,4′S*,5R*)-8-benzyl-4′-(2-benzyloxy-5-trifluoromethoxyphenyl)-6-(tert-butoxycarbonyl)-2′,3′,4′,5′-tetrahydro-1-phenylspiro[8-azabicyclo[3.2.1]octane-2,2′-furan] (Description 28; 1.065 g, 1.52 mmol), 10% palladium on charcoal (340 mg, 0.32 mmol) and ethanol (20 ml) was stirred under hydrogen atmosphere (1 atm) at +65° C. for 1.5 hour. The reaction mixture was cooled to room temperature, flushed with nitrogen gas and filtered through a pad of Celite™. The filtrate was concentrated to give the title compound (900 mg, 97%).

Provenance & Evidence