Acetic Acid → 1-Boc-4-AP

Participants

Reaction Steps

To a solution of Boc-4-piperidone (4.0 g, 20 mmol), aniline (1.9 ml, 20 mmol), and acetic acid, glacial (1.4 ml, 24 mmol) in dichloroethane (60 mL) was added sodium triacetoxyborohydride (6.0 g, 28 mmol) portionwise at RT. The suspension was stirred at RT for 24 h, diluted with water and extracted with dichloromethane. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by ISCO using 0-30% EtOAc in Hexanes to give tert-butyl 4-(phenylamino)piperidine-1-carboxylate (2.5 g, 45% yield).

Provenance & Evidence