Sodium hydride → HCID 86586687, compound

Participants

Reaction Steps

Sodium hydride (60% in oil, 100 mg, 2.5 mmol) was added to a stirred mixture of 1R*,2R*,5S*,6R*)-6-cyano-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]octan-2-ol (Description 24; 400 mg, 1.49 mmol), 3,5-bis(trifluoromethyl)benzyl bromide (1 ml, 5.45 mmol) and 18-crown-6 (87 mg, 0.33 mmol) in THF (5 ml) at room temperature. The reaction mixture was stirred for 22 hours, quenched with water and extracted into dichloromethane. The combined organic extracts were washed with water, dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate) to give the title compound (530 mg, 72%).

Provenance & Evidence