Hydrochloric Acid → HCID 70009752, compound

Participants

Reaction Steps

(1R*,2R*,5S*)-2-amino-8-benzyl-1-phenyl-8-azabicyclo[3.2.1]octane (Description 9; 156 mg, 0.53 mmol) and 2-methoxy-5-(trifluoromethoxy)benzaldehyde (132 mg, 0.6 mmol) were dissolved in 1,2-dichloroethane (10 mL) and acetic acid (35 μL), and treated with sodium triacetoxyborohydride (127 mg, 0.6 mmol). The suspension formed was stirred at ambient temperature for 16 hours, then quenched with saturated aqueous sodium hydrogen carbonate solution (50mL). The mixture was extracted with dichloromethane (2×50 mL) and the extracts were dried (MgSO4), then concentrated. Purification of the residue gave the desired free base which was taken up in ethyl acetate (10 mL) and treated with ethereal hydrogen chloride (1M, 2 mL). The solid formed was recovered by filtration and recrystallized from methanol/diethyl ether to give the title compound as a white solid (178 mg, 0.3 mmol).

Provenance & Evidence