Benzyl chloroformate → Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate

Participants

Reaction Steps

DIEA (4.6 mL, 3.4 g, 26 mmol) was added to a solution of 4-(hydroxymethyl)piperidine (2.00 g, 17.4 mmol) dissolved in CH2Cl2 (20 mL). The solution was cooled in an ice bath and benzyl chloroformate (2.5 mL, 3.0 g, 18 mmol) was added dropwise over 10 min. After warming to RT and stirring for 96 h, the mixture was diluted with EtOAc (50 mL) and washed in succession with 25 mL each of saturated aq. NaHCO3, 2 N HCl, saturated aq. NaHCO3, and saturated aq. NaCl. The organic layer was dried (Na2SO4), decanted, and evaporated to give 4.14 g of 1-(benzyloxycarbonyl)-4-(hydroxymethyl)piperidine.

Provenance & Evidence