反应详情

To a THF solution at 0° C. under argon is added 2-anilino-6-quinoxalinol (0.23 g, 0.97 mmol), (S)-(+)-3-hydroxytetrahydrofuran (0.086 mL, 1.3 mmol), and triphenylphosphine (0.31 g, 1.2 mmol). DEAD (0.18 mL, 1.2 mmol) is added portionwise. The reaction is allowed to warm to room temperature and stirred for 1.5 hours. The mixture is concentrated and partitioned between EtOAc and H2O. The organic layer is washed with H2O, brine, dried (MgSO4), and concentrated. The resulting yellow oil is chromatographed (50% EtOAc/hexanes) and taken up in Et2O/IPA. HCl/Et2O solution is added dropwise and the resulting red-orange powder is dried in vacuo. The powder is free-based by stirring in MeOH with washed (3×H2O, 5×MeOHM basic ion exchange resin. The mixture is stirred 30 minutes, filtered, concentrated, and recrystallized from EtOAc/hexanes to provide, in two crops, the product (m.p. 173-175° C.). Anal. Calcd. for C18H17N3O2: C, 70.35; H, 5.57; N, 13.67; Found: C, 70.19; H, 5.60; N, 13.66.

1. concentrationThe mixture is concentrated
2. custompartitioned between EtOAc and H2O
3. washThe organic layer is washed with H2O, brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. customThe resulting yellow oil is chromatographed (50% EtOAc/hexanes)
7. additionHCl/Et2O solution is added dropwise
8. customthe resulting red-orange powder is dried in vacuo
9. stirringby stirring in MeOH
10. washwith washed (3×H2O, 5×MeOHM basic ion exchange resin
11. stirringThe mixture is stirred 30 minutes
12. filtrationfiltered
13. concentrationconcentrated
14. customrecrystallized from EtOAc/hexanes
15. customto provide, in two crops