1-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 39.2 gm (152 mMol) ethyl 1-tert-butoxycarbonylpiperidine-4-carboxylate in 600 mL diethyl ether were cautiously added 6.1 gm (152 mMol) lithium aluminum hydride in portions. The reaction mixture was stirred for about 1.5 hours after the addition was complete and was then carefully quenched with water. The reaction mixture was partitioned between diethyl ether and 5 N sodium hydroxide. The organic phase was washed with saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure to provide about 24 gm of a waxy solid. This solid was crystallized from a mixture of diethyl ether and hexane to provide 11.7 gm (36%) of 1-tert-butoxycarbonyl-4-hydroxymethylpiperidine as a white solid.

Provenance & Evidence