Dimethyl Sulfoxide → 1-Boc-4-cyano-4-(4-pyridinyl)-piperidine

Participants

Reaction Steps

4-Cyanomethylpyridinium hydrochloride (1.0 g, 6.5 mmol), 2.0 g tert-butyl bis(2-chloroethyl)carbamate (J. Med. Chem. 1992, 35, 11, 2033-2039) (8.1 mmol), 9.1 g caesium carbonate (28 mmol) and 20 ml DMSO were combined in a round bottom flask and stirred at room temperature for 20 hours. The reaction mixture was diluted with ethyl acetate and the organic layer washed with water, then brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The product was purified by column chromatography on silica, using a gradient from 10% to 100% ethyl acetate in hexanes as eluent. 778 mg of the title compound were isolated as an oil (42% yield)

Provenance & Evidence