Triethylamine → tert-butyl N-(3-azidopropyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,1-dimethylethyl (3-hydroxypropyl)carbamate (1.612 g, 9.2 mmol) in toluene (40 mL) cooled with an ice bath was added triethylamine (1.282 mL, 9.20 mmol) then methanesulfonyl chloride (0.717 mL, 9.20 mmol) and the resulting mixture was stirred for 15 min. Tetrabutylammonium bromide (0.297 g, 0.920 mmol) was then added followed by a solution of sodium azide (5 g, 77 mmol) in water (20 mL) and the resulting mixture was stirred at 60° C. for 7 h then cooled to room temperature and diluted with Et2O (150 mL). The two layers were separated and the organic phase was washed with water then brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by SP4 using a 25 G silica cartridge gave 1,1-dimethylethyl (3-azidopropyl)carbamate (1.27 g, 6.34 mmol, 68.9% yield) as a colourless oil.

Provenance & Evidence