Sodium hydride → HCID 86586774, compound

Participants

Reaction Steps

(1R*,2R*,5S*,6S*)-8-benzyl-6-fluoro-6-[1-(2-methoxyethoxymethyl)-1H-tetrazol-5-yl]-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol (Description 45; 205 mg, 0.44 mmol) was added to a stirred mixture of sodium hydride (60% in oil, 60 mg, 1.5 mmol, washed twice with iso-hexane) in THF (2 ml) followed by 18-crown-6 (40 mg, 1.5 mmol) and 3,5-bis(trifluoromethyl)benzyl bromide (0.4 ml, 2.16 mmol) at room temperature. The reaction mixture was warm up to reflux and stirred at room temperature overnight, then quenched with saturated aqueous NH4Cl and extracted into diethyl ether. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 10-70%) to give the title compound (303 mg, 97%).

Provenance & Evidence