Citric Acid → 4-[2-(t-Butyldimethyl silanyloxy)ethyl]-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carboxaldehyde

Participants

Reaction Steps

To a solution of 4-[2-(t-butyldimethyl silyloxy)ethyl]-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrile (600 mg) in 1,2-dimethoxyethane (12 mL) was added diisobutylaluminum hydride (1.0 M toluene solution, 6.39 mL) at 0° C. The mixture was stirred for 4 hours. To the reaction solution was added aqueous citric acid solution and extracted with ethyl acetate. The organic layer was sequentially washed with aqueous citric acid solution, water and brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (526 mg). Yield: 87%.

Provenance & Evidence