Benzyl Bromide → 1-Boc-4-(hydroxymethyl)-4-[(benzyloxy)methyl]piperidine

Participants

Reaction Steps

Finely ground potassium hydroxide (248 mg, 44 mmol) was added to a stirred, cooled (10° C.) solution of 1,1-dimethylethyl 4,4-bis(hydroxymethyl)-1-piperidinecarboxylate (Description 67, 1.83 g, 7.4 mmol), 18-crown-6 (196 mg, 0.74 mmol) and benzyl bromide (884 μL, 7.4 mmol) in tetrahydrofuran (80 mL) and the mixture was stirred at room temperature for 16 hours. Brine (40 mL) was added and the layers were separated. The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (80:20 increasing to 50:50) to give the title compound (1.0 g, 40%). m/z (ES+) 336 (M+1).

Provenance & Evidence