Acetic Acid → tert-Butyl 4-(benzyl(methyl)amino)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of N-benzylmethylamine (648 μL, 5.02 mmol) and 1-tert-butoxycarbonyl-4-piperidone (500 mg, 2.51 mmol) in THF (8 mL) was added sodium triacetoxyborohydride (798 mg, 3.76 mmol) followed by acetic acid (144 μL, 2.5 mmol) and the reaction stirred at rt for 40 h. Solvent was removed in vacuo and the residue partitioned between ethyl acetate (15 mL) and water (15 mL). The organic layer was washed with sodium bicarbonate solution (2×15 mL) then brine (2×20 mL), dried (MgSO4) and the solvent removed in vacuo. The crude material was purified by chromatography using ethyl acetate/petroleum ether (2:1) as the eluent to give the title compound as yellow oil. m/z (ES+)=305.32 [M+H]+.

Provenance & Evidence