Methyl iodide → 1-Tert-butoxycarbonyl-4-(4-chlorophenyl)-4-methoxypiperidine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-tert-butoxycarbonyl-4-(4-chlorophenyl)-4-hydroxypiperidine (1.0 g) in N,N-dimethyl formamide (10 ml) was added sodium hydride (0.14 g) under ice cooling. Then the reaction mixture was stirred for 30 minutes at room temperature and for 2 hours at 60° C. To the reaction mixture was added iodomethane (4.0 ml) at 60° C. After stirring for 6 hours at 60° C., the reaction mixture was poured into a mixture of ethyl acetate and water. The organic layer was successively washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (10:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give 1-tert-butoxycarbonyl-4-(4-chlorophenyl)-4-methoxypiperidine (0.75 g).

Provenance & Evidence