Sodium Bicarbonate → HCID 86586085, compound

Participants

Reaction Steps

(1R*,2R*,5S*)-2-Amino-1-phenyl-8-azabicyclo[3.2.1]octane (Description 6; 77 mg, 0.38 mmol) and 2-chloro-5-(trifluoromethoxy)benzaldehyde (Description 27; 120 mg, 0.53 mmol) were dissolved in 1,2-dichloroethane (5 mL) and acetic acid (1mL), then treated with sodium triacetoxyborohydride (128 mg, 0.6 mmol). The suspension was stirred at room temperature for 16 hours, then diluted with methanol (5 mL). Sodium cyanoborohydride was added (200 mg, 0.9 mmol) and this solution stirred for a further 16 hours at ambient temperature. The resulting mixture was poured into saturated aqueous sodium hydrogen carbonate solution (50 mL) and extracted with dichloromethane (2×50 mL). The extracts were dried (MgSO4) and concentrated to yield a gum, which was purified by silica chromatography. The pure free base was dissolved in ethyl acetate (10 mL) and treated with ethereal hydrogen chloride (2 mL, 1M). The solid formed was removed by filtration, washed with diethyl ether and dried to give the title compound as a solid (46 mg, 0.1 mmol).

Provenance & Evidence