Benzyl chloroformate → Benzyl ethyl piperidine-1,3-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

To a room temperature solution of 4.05 g (25.8 mmoles) of ethyl nipecotate and 4.33 g (51.5 mmoles) of NaHCO3 in water (26 mL) was added benzyl chloroformate (4.1 mL, 28.3 mmol). The reaction mixture was stirred at 23° C. under an atmosphere of N2 overnight. The crude products were diluted with water, extracted with Et2O, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography employing a solvent gradient (hexane→70:30 hexane:EtOAc) to yield the title compound as a clear colorless oil.

Provenance & Evidence