Sodium Hydroxide → HCID 59433298, compound

Participants

Reaction Steps

A solution of tert-butyl 1-benzyl-4-methylpiperidine-4-carboxylate (4.7 g, 18 mmol) in diethyl ether (47 mL) was cooled at 0° C. and to this was added lithium tetrahydroaluminate (990 mg, 25 mmol) portion-wise. The reaction mixture was warmed to ambient temperature and stirred vigorously for 1 hour. The mixture was then cooled to 0° C. and a 1N solution of sodium hydroxide (6 mL) was added dropwise to the reaction mixture producing a white precipitate. The mixture was filtered and the solids were washed with ethyl acetate (100 mL). The combined filtrate was separated and the aqueous portion was extracted with ethyl acetate (2×50 mL). The combined organic portions were dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 80 g, ISCO, 45-100% ethyl acetate in heptane) to afford the title compound as a white solid, which was used in the next step without any further purification (2.7 g, 67%).

Provenance & Evidence