Triethylamine → tert-Butyl (2-azidoethyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,1-dimethylethyl (2-hydroxyethyl)carbamate (1.483 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 5 min at this temperature then tetrabutylammonium bromide (0.297 g, 0.920 mmol) was added followed by a solution of sodium azide (5 g, 77 mmol) in water (20 mL). The resulting mixture was stirred at 60° C. for 3 h then cooled to room temperature and diluted with Et2O (150 mL). The organic layer was washed with water then brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by SP4 using a 50G silica cartridge gave 1,1-dimethylethyl (2-azidoethyl)carbamate (456 mg, 2.449 mmol, 26.6% yield) as a colourless oil.

Provenance & Evidence