Lithium Hexamethyldisilazide → 4-[2-(t-Butyldimethyl silyloxy)ethyl]-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrile (1.00 g) in tetrahydrofuran (10 mL) was added lithium bis(trimethylsilyl)amide (3.21 mL) at −15° C. To the reaction solution was added (2-bromoethoxy)-t-butyldimethyl silane (689 μL). The mixture was stirred at 0° C. for 3 hours. To the reaction solution was added brine and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure and the obtained residue was purified by column chromatograph on silica gel to give the title compound (1.23 g). Yield: 82%.

Provenance & Evidence