Sodium Azide → tert-butyl [(1R,2R)-2-azido-3,3-difluorocyclohexyl]carbamate

Participants

Reaction Conditions

Reaction Steps

is A solution of (1S,6R)-6-[(tert-butoxycarbonyl)amino]-2,2-difluorocyclohexyl trifluoromethanesulfonate (2.32 g, 6.05 mmol) and sodium azide (2.36 g, 36.3 mmol) in DMF was sealed and heated to 100° C. for 3 hours in a microwave reactor. The reaction was partitioned between water and ethyl acetate. The organics were washed with water, dried over magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography afforded the title compound as a white solid: 1H NMR (500 MHz, CDCl3) δ 4.75 (m, 1H); 3.98 (br s, 1H); 3.88 (m, 1H); 1.96 (m, 2H); 1.70 (m, 2H); 1.46 (s, 9H); 1.37 (m, 2H). tert-Butyl[(1R,6S)-6-azido-2,2-difluorocyclohexyl]carbamate was also obtained from this procedure: 1H NMR (500 MHz, CDCl3) 4.82-4.80 (d, 1H); 3.93-3.89 (dt, 1H); 3.31-3.27 (m, 1H); 2.24-2.19 (m, 1H); 2.13-2.10 (m, 1H); 1.86-1.67 (m, 2H); 1.55-1.52 (m, 2H); 1.48-1.41 (m, 11H). 19F NMR (CDCl3, 564 MHz) −102.2-−102.7 (d, 1F); −113.9-−114.5 (m, 1F).

Provenance & Evidence