Sodium hydride → tert-Butyl 4-(5-cyanopyridin-2-yloxy)piperidine-1-carboxylate

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Reaction Conditions

Reaction Steps

To a solution of 1-(t-butyloxycarbonyl)-4-piperidinol (600 mg) in dry DMF (20 mL) was added sodium hydride (0.24 g, 50% dispersion in oil) and stirred under argon for 1 hour. 2-Chloro,5-cyanopyridine (0.44 g) was added and the mixture was heated at 70° C. overnight. The reaction was quenched by pouring into water and extracted with diethyl ether. The extract was washed with water, brine, dried (MgSO4) and evaporated. The residue was then chromatographed on silica gel eluting with a mixture of dichloromethane (25%) in isohexane increasing to dichloromethane. The residue was recrystallised from isohexane to afford 1-(t-butyloxycarbonyl),4-(5-cyano,2-pyridyloxy)piperidine (400 mg) as a colourless crystalline solid; NMR: (CDCl3) 1.46 (s,9H), 164-182 (m,2H), 1.92-2.09 (m,2H), 3.21-3.36 (m,2H), 3.70-3.84 (m,2H), 5.28 (m,1H), 6.78 (d,1H), 7.77 (dd,1H): MS: m/z 304 (MH)+.

Provenance & Evidence