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

Participants

Reaction Conditions

Reaction Steps

A solution of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (60.0 mmol, 1.0 eq.) in dry THF (80 ml) was added dropwise to a suspension of LAH (90.0 mmol, 1.5 eq.) in THF (120 ml) at 0° C. After addition of the reagent was completed the reaction mixture was stirred at 25° C. for 1 h. The reaction mixture was quenched by very slow addition of a mixture of THF-water (9:1, 36 ml) and 10% NaOH solution (7.2 ml). The mixture was then filtered through celite and filtrate was concentrated to yield the desired product as a white solid which was used in the next step without further purification. Yield: 77%

Provenance & Evidence