Benzyl Bromide → HCID 70244349, compound

Participants

Reaction Steps

To a solution of trans-N-t-butoxycarbonyl-4-(3-methylphenyl)-3 hydroxy piperidine (131 mg, 0.449 mmol), in DMF (2 ml) at 0° C. was added sodium hydride (27 mg of a 60% dispersion in mineral oil, 0.890 mmol). After 10 min, benzyl bromide (0.107 ml, 0.890 mmol) was added and the reaction allowed to warm to room temperature over 16 hrs. The reaction was quenched by the addition of saturated NH4Cl solution (5 ml) and extraction with EtOAc. The organic extracts were washed with brine and dried (MgSO4) and the solvent evaporated in vacuo. Chromatography of the residue (SiO2, gradient elution, 10-15% EtOAc in hexanes) afforded the title compound as an oil.

Provenance & Evidence