Cyanuric chloride → tert-Butyl 4-cyano-4-isopropylpiperidine-1-carboxylate

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Reaction Steps

To a solution of tert-butyl 4-(aminocarbonyl)-4-isopropylpiperidine-1-carboxylate (100 mg, 0.370 mmol) in dimethylformamide (2 ml) was added cyanuric chloride (34.1 mg, 0.185 mmol). After stirring over the weekend at room temperature, the mixture was diluted with 10 ml of water, and 20 ml of ethyl acetate. The phases were separated and the aqueous phase was extracted with ethyl acetate (2×15 ml). The combined organics were washed with 10 ml each of saturated sodium bicarbonate solution and brine, dried (sodium sulfate), and then concentrated to provide the title compound (93 mg, 0.369 mmol, 100% yield). Mass spectrum (ESI) 153.2.0 (M-Boc).

Provenance & Evidence