Hydrochloric Acid → HCID 86586746, compound

Participants

Reaction Steps

(1R*,2R*,5S*,6R*)-8-Benzyl-2-{(1S*)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-1-phenyl-6-(1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane (Example 133; 185 mg, 0.31 mmol) was dissolved in methanol (5 ml) and 2N hydrochloric acid (0.5 ml) and 10% palladium hydroxide (50 mg) added. The mixture was hydrogenated at 45 psi for 1.5 hours. The reaction mixture was filtered then concentrated in vacuo. The residue was partitioned between saturated sodium hydrogen carbonate solution and dichloromethane and the organics removed, dried (MgSO4) and concentrated in vacuo. The oil was purified by flash column chromatography [5% methanol in dichloromethane] and the hydrochloride salt was made by adding 1 equivalent of hydrogen chloride in diethyl ether (1.0M) to a solution in diethyl ether and the title compound filtered and dried in vacuo at 60° C. (27 mg, 16%).

Provenance & Evidence