Water → 1,1-Dimethylethyl 4-azido-1-piperidinecarboxylate

Participants

Reaction Steps

To a solution of 45.3 g (172 mmol) of 4-bromo-1-t-butoxycarbonylpiperidine in 750 mL of DMF was added 22.3 g (343 mmol) of sodium azide and 2.5 g (17 mmol) of sodium iodide. The reaction was stirred at rt for 24 h and then at 60° C. for 4 h. The mixture was poured into water containing 20 mL of sodium bicarbonate and extracted twice with 1:1 ether:hexanes. The organic layers were each washed with a portion of water and brine, dried over sodium sulfate, combined and concentrated. The residue was purified by FC eluting with 5-10% ethyl acetate in hexanes to afford 39 g of title compound having a trace of elimination byproduct.

Provenance & Evidence