反应详情

温度

0 °C

Triphenylphosphine (1.81 g, 6.9 mmol, 1.2 eq) was dissolved in anhydrous THF (30 mL) and cooled to 0° C. To this solution was added diispropylazodicarbox-ylate (1.36 mL, 6.9 mmol, 1.2 eq). The reaction was stirred for 30 minutes at 0° C. and (R)-1-(2-chloro-8-fluoroquinolin-3-yl)ethanol (1.3 g, 5.7 mmol) in 30 mL of THF was added, followed by diphenylphosphoryl azide (1.37 mL, 6.3 mmol, 1.1 eq). The reaction was allowed to warm to rt and stir at rt overnight. The reaction was deposited on silica gel and concentrated. Purification by column chromato-graphy (3% etoac in hexanes) afforded (S)-3-(1-azidoethyl)-2-chloro-8-fluoro-quinoline. 1H NMR (400 MHz, CDCl3) δ ppm 8.30 (d, J=1.2 Hz, 1H), 7.67 (br d, J=8.22 Hz, 1H), 7.54 (td, J=7.8, 4.7 Hz, 1H), 7.45 (ddd, J=10.2, 7.8, 1.2 Hz) 5.22 (q, J=6.7 Hz, 1H), 1.68 (d, J=6.7 Hz, 3H). Mass Spectrum (ESI) m/e=250.9 (M+1).

1. additionTo this solution was added diispropylazodicarbox-ylate (1.36 mL, 6.9 mmol, 1.2 eq)
2. temperatureto warm to rt
3. stirringstir at rt overnight
4. concentrationconcentrated
5. customPurification by column chromato-graphy (3% etoac in hexanes)