Benzyl Bromide → HCID 18374750, compound

Participants

Reaction Steps

NaH (60% oil dispersion, 53 mg, 1.3 mmol) was added in portions to a solution of 1-(tert-butoxycarbonyl)-4-(hydroxymethyl)piperidine (240 mg, 1.1 mmol) and benzyl bromide (0.40 mL, 0.58 g, 0.33 mmol) in DMF (2.0 mL). After 1 h, additional NaH (60% oil disperison, 15 mg, 0.38 mmol) was added. After a total of 2.25 h, the mixture was quenched with water and extracted with EtOAc. The organic layer was washed with saturated aq. NaCl, dried (Na2SO4), and evaporated. Purification by flash column chromatogaraphy on silica gel, eluting with 5-10% EtOAc in hexane gave 167 mg of 4-(benzyloxymethyl)-1-(tert-butoxycarbonyl)piperidine. A portion (160 mg, 0.55 mmol) of this intermediate was dissolved in CH3OH (2.0 mL) and a solution of HCl (2 N in ether, 2.0 mL, 4 mmol) was added. The mixture was stirred overnight at RT and evaported to give the title compound as a white solid.

Provenance & Evidence