Hydrochloric Acid → Benzyl 4-Hydroxy-1-piperidinecarboxylate

Participants

Reaction Steps

Benzyl chloroformate (8.55 mL; 60 mmol) was added drop wise over a period of 30 min to a well stirred chilled mixture of piperidin-4-ol (5 g; 49.44 mmol), 1N aqueous NaOH (60 mL; 60 mmol) and dioxane (60 mL). The mixture was stirred for 30 min. at room temperature, treated with water, acidified with conc. HCl to pH 2 and extracted with EtOAc. The EtOAc layer was washed with water, brine, dried (Na2SO4), concentrated and purified using flash chromatography (silica gel, 50% CH2Cl2 in PE 60-80° C., 10% CH3CN+2% MeOH in chloroform). Yield, 12.5 g (99%), oil; MS (CI): 236 (M++1). 218, 192, 174, 91.

Provenance & Evidence