Aluminium lithium hydride → tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (84 mg, 2.2 mmol) in THF (5 mL), a solution of tert-butyl 4-cyano-4-hydroxypiperidine-1-carboxylate (200 mg, 0.88 mmol, step 1 of Example 22) in THF (1 mL) was added dropwise at 0° C. The mixture was stirred for 1 h at that temperature and Na2SO4.10H2O (400 mg) was added slowly, and the mixture was stirred for 5 h at room temperature. The mixture was filtered though a pad of Celite, washed with CH2Cl2 (20 mL×2), the filtrate was concentrated to give clear colorless oil. The residue was chromatographed on a column of silica gel eluting with CH2Cl2/MeOH/NH4OH (14:1:0.1) to give 120 mg (59%) of the title compound as white solid.

Provenance & Evidence