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

Participants

Reaction Conditions

Reaction Steps

To a solution of N-t butyloxycarbonyl-4-bromopiperidine (8.8 g, 33.5 mmol) in N,N-dimethylformamide (50 ml) was added sodium azide (6.5 g, 100.4 mmol) and the reaction mixture was heated at 60° C. for 18 hrs., cooled to room temperature, poured into water (200 ml) and extracted with dichloromethane (2×200 ml). The combined organic layers were washed with brine (2×50 ml), dried (MgSO4), filtered and concentrated under vacuum, to give the required product (6.0 g). 1H NMR (CDCl3) δ 1.28 (9H, s), 1.56 (2H,m), 1.88 (2H,m), 3.10 (2H,m), 3.58 (1H,m), 3.82 (2H,m).

Provenance & Evidence