Methyl iodide → Tert-butyl 4-methoxypiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a suspension of 60% sodium hydride (939 mg) in dimethylformamide (30 ml) was added 1-t-butoxycarbonyl-4-hydroxypiperidine (3.15 g) under ice-water cooling and the mixture was stirred at 0° C. for 0.5 hour. To the solution was added methyl iodide (1.17 ml) under ice-water cooling and the mixture was stirred at 0° C. for 1 hour. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (3:1) to give 1-t-butoxycarbonyl-4-methoxypiperidine as colorless oil (2.84 g).

Provenance & Evidence