tert-Butanol → Benzyl 3-(tert-butoxycarbonylamino)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 1-[(benzyloxy)carbonyl]-3-piperidinecarboxylic acid (3.00 g, 11.4 mmol) and Et3N (1.56 mL, 11.4 mmol) in t-BuOH (30 mL) was added diphenyl phosphoryl azide (DPPA) (2.46 mL, 11.4 mmol), and the mixture was refluxed for 21 hrs. After cooled to room temperature, the mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and a saturated aqueous NaHCO3 solution. The organic phase was washed with a saturated aqueous NaHCO3 solution and brine, dried over Na2SO4, and concentrated under reduced pressure. Purification by column chromatography on silica gel (hexane/ethyl acetate=4/1 to 3/1) gave benzyl 3-[(tert-butoxycarbonyl)amino]-1-piperidinecarboxylate as a solid (2.22 g, yield; 58%).

Provenance & Evidence