(1R*,2R*,4'S*,5S*,6R*)-8-Benzyl-4'-(2-benzyloxy-5-trifluoromethoxyphenyl)-2',3',4',5'-tetrahydro-1-phenyl-6-phenylsulfonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan] → (1R*,2R*,4'S*,5S*,6R*)-2',3',4',5'-Tetrahydro-4'-(2-hydroxy-5-trifluoromethoxyphenyl)-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2'-furan]

Participants

Reaction Steps

A mixture of (1R*,2R*,4′S*,5S*,6R*)-8-benzyl-2′,3′,4′,5′-tetrahydro-4′-(2-benzyloxy-5-trifluoromethoxyphenyl)-1-phenyl-6-phenylsulphonylspiro[8-azabicyclo[3.2.1]octane-2,2′-furan](Description 16; 2.2 g, 2.97 mmol), 5% palladium on charcoal (3 g, 1.4 mmol) and ethanol (55 ml) was stirred under hydrogen atmosphere (1 atm) at +70° C. for 70 minutes. 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 (1.77 g, quant.).

Provenance & Evidence