Sodium hydride → (1R*,2R*,5R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane

関与物質

反応手順

Sodium hydride (60% in oil, 90 mg, 2.25 mmol) was washed twice with THF and treated with a solution of (1R,2R,5R)-8-benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol (Description 53; 79 mg, 0.25 mmol), 3,5-bis(trifluoromethyl)benzyl bromide (350 mg, 1.14 mmol), 18-crown-6 (110 mg, 0.41 mmol) in THF (5 ml). The reaction mixture was stirred at room temperature for 24 hours, 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 (165 mg).

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