Methanol → Tert-butyl 2-(1-tert-butylpiperidin-4-yl)hydrazinecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 2-(1-tert-butylpiperidin-4-ylidene)hydrazinecarboxylate (400 mg, 1.49 mmol) in THF (40 mL) was added DIBAl-H (15 mL, 15 mmol) under nitrogen atmosphere. The resulting mixture was stirred at 25° C. overnight. Methanol (5 mL) was added at −78° C. After being stirred at room temperature for 1 h, water (10 mL) was added. The solid was filtered off and washed with EtOAc. The combined filtrate was partitioned and extracted with EtOAc (3×50 mL), dried over Na2SO4, and concentrated. The residue was purified by silica gel chromatography eluting with EtOAc/petroleum ether (1:10) to give tert-butyl 2-(1-tert-butylpiperidin-4-yl)hydrazinecarboxylate (350 mg, 87% yield) as colorless oil. LCMS (ESI) m/z: 272.4 [M+H+].

Provenance & Evidence