Hydrochloric Acid → HCID 58188261, compound

Participants

Reaction Steps

To a stirred solution of (S)-2-azido-2-(6-(difluoromethyl)pyridin-3-yl)ethanol (1 g, 4.67 mmol) in 15 mL of THF was added PPh3 (2.45 g, 9.39 mmol). The resulting reaction mixture was stirred for 3 h, treated with 0.5 mL of water and stirred for 16 h. After completion of the reaction, the reaction mixture was treated with 2N HCl (15 mL) and extracted with EtOAc. The aqueous layer was treated with aq. NH3 and the volatiles were evaporated to afford a residue. Purification of the residue by column chromatography (small pad of neutral Al2O3, aq. NH3/MeOH/CH2Cl2, 1:14:85) afforded the title compound (0.74 g, 85% yield). MS: 189 [M+1]+; 1H-NMR (300 MHz, CD3OD): 8.72 (s, 1H), 8.09 (d, 1H, J=8.3 Hz), 7.75 (d, 1H, J=8.3 Hz), 6.73 (t, 1H, J=55.0 Hz), 4.39-4.43 (m 1H), 3.90 (dd, 1H, J=10.9, 4.7 Hz), 3.80 (dd, 1H, J=10.9, 6.2 Hz).

Provenance & Evidence