3,5-Dichlorobenzylic alcohol → 3,5-Dichlorobenzyl 4-(tert-butoxycarbonylamino)piperidine-1-carboxylate

Participants

Reaction Steps

A mixture comprising tert-butyl piperidin-4-ylcarbamate (5 g, 24.97 mmol), 3,5-dichlorobenzyl alcohol (4.42 g, 24.97 mmol) and carbonyldiimidazole (4.05 g, 24.97 mmol) in DMF (83 ml) was heated at 50° C. with stirring for 3 days. The resulting mixture was concentrated under reduced pressure. The crude material was redissolved in EtOAc and washed with 1M HCl, a saturated solution of sodium bicarbonate and brine. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The mixture was purified by chromatography on silica eluting with 50-100% EtOAc in iso-hexane and then 1-10% MeOH in EtOAc to afford the title product;

Provenance & Evidence