Sodium Azide → Tert-butyl n-[1-(azidomethyl)undecyl]-carbamate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl N-[1-(R/S)-(iodomethyl)undecyl]carbamate 62 (250 mg, 0.608 mmol) was dissolved in abs. DMF (10 ml). Sodium azide (79.0 mg, 1.22 mmol) was added to the solution, which was subsequently stirred at 110° C. for 12 hours. Following evaporation, the residue was taken up in CH2Cl2 (50 ml) and was washed with NaHCO3(sat, aq) (1×50 ml). The organic phase was dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography in hexane:ether 10:1 (v/v) to give 63 (100 mg, 54%).

Provenance & Evidence