反应详情

2,6-Lutidine (6.9 mL, 59.5 mmol) was added to a solution of (R)-8-(benzyloxy)-5-(2-bromo-1-hydroxyethyl)quinolin-2(1H)-one (10.1 g, 27.0 mmol) in DCM (100 mL) at 0° C. The reaction mixture was stirred for 5 minutes and then tert-butyldimethylsilyl trifluoromethanesulfonate (13.0 mL, 56.8 mmol) was added dropwise over 15 minutes. The mixture was stirred at 0° C. for 30 minutes, followed by RT overnight. After this time the reaction was quenched with saturated aqueous sodium bicarbonate solution and extracted with DCM (×3). The combined organic extracts were dried (magnesium sulfate), filtered and concentrated under reduced pressure. Iso-hexane (500 mL) was added to the crude material and the resulting solid collected by filtration. The solid was recrystallised from ethyl acetate and petroleum ether (40:60) to afford the title compound (11.3 g, 85%).

1. stirringThe mixture was stirred at 0° C. for 30 minutes
2. waitfollowed by RT overnight
3. customAfter this time the reaction was quenched with saturated aqueous sodium bicarbonate solution
4. extractionextracted with DCM (×3)
5. dry with materialThe combined organic extracts were dried (magnesium sulfate)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. additionIso-hexane (500 mL) was added to the crude material
9. filtrationthe resulting solid collected by filtration
10. customThe solid was recrystallised from ethyl acetate and petroleum ether (40:60)