Triethylamine → (R)-tert-Butyl 1-azido-3-ethoxypropan-2-ylcarbamate

Participants

Reaction Steps

Methanesulfonyl chloride (0.851 mL, 10.95 mmol) in DCM (1 mL) was added to a solution of (R)-tert-butyl 1-ethoxy-3-hydroxypropan-2-ylcarbamate (1.6 g, 7.30 mmol) and Et3N (1.538 mL, 10.95 mmol) in DCM (10 mL) at 0° C. After stirring at RT for 1 h, the mixture was diluted with EtOAc. The organic layer was washed with saturated aq NaHCO3 solution, dried, and concentrated in vacuo. The residue was dissolved in DMF (10.00 mL). Sodium azide (2.372 g, 36.5 mmol) and tetrabutylammonium iodide (0.270 g, 0.730 mmol) were added, and the reaction mixture was stirred at 75° C. for 4 h. After cooling to RT, the mixture was diluted with EtOAc. The organic layer was washed with saturated aq NaHCO3, dried, and concentrated in vacuo to give the title compound (1.2 g, 67%). [M+H] calc'd for C10H20N4O3, 245; found, 245.

Provenance & Evidence