Sodium Azide → 1,1-Dimethylethyl 4-azido-1-piperidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

N-tert-butyloxycarbonyl-4-piperidinemethanesulfonate (10.0 g, 36 mmol) was dissolved in DMF (100 mL), sodium azide (NaN3, 7.0 g, 108 mmol) was added, the reaction mixture was warmed to 100° C., and the reaction was performed overnight. The solvent in the resultant mixture was evaporated under reduced pressure, water (100 mL) and ethyl acetate (100 mL) were added, the organic phase was separated, washed with water (100 mL×2) and saturated brine successively, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure to remove ethyl acetate so as to yield the target product as light yellow liquid (8.2 g, 36 mmol; yield=100%). The crude produce was directly used for the reaction in the next step.

Provenance & Evidence