Sodium hydride → HCID 86586781, compound

Participants

Reaction Steps

Sodium hydride (60% in oil, 67 mg, 1.67 mmol) was washed twice with THF and treated with a solution 1S,2S,5S)-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]octan-2-ol (Description 57; 116 mg, 0.47 mmol), 3,5-bis(trifluoromethyl)benzyl bromide (430 mg, 1.4 mmol), 18-crown-6 (33 mg, 1.25 mmol) in THF (2 ml). The reaction mixture was stirred at room temperature overnight, quenched with saturated aqueous NH4Cl and extracted into diethyl ether. The combined organic extracts were washed with water, dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:diethyl ether) to give the title compound.

Provenance & Evidence