Acetic Acid → (1R*,2R*,5S*,6R*)-6-Acetamidoazido-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane hydrochloride

Participants

Reaction Steps

(1R*,2R*,5S*,6R*)-6-Acetamidoazido-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane (Example 104; 240 mg, 0.40 mmol) was dissolved in ethyl acetate (10 ml) and glacial acetic acid (1 ml) then 10% palladium hydroxide (30 mg) added and the mixture hydrogenated at 45 psi overnight. The reaction mixture was then filtered and the mixture further hydrogenated with fresh catalyst (30 mg) overnight. The reaction mixture was filtered then concentrated in vacuo, basified (saturated sodium hydrogen carbonate solution), extracted with dichloromethane (×3), dried (MgSO4), and concentrated in vacuo. The crude product was purified by flash column chromatography [10% methanol in dichloromethane] to give an oil which when concentrated with iso-hexane gave a white solid. The hydrochloride salt was made by dissolving in diethyl ether and adding 1 equivalent of hydrogen chloride in diethyl ether. The title compound was filtered off and dried in vacuo at 60° C.

Provenance & Evidence