反应详情

To a mixture of (tert-butoxy)-N-{[4-fluoro-3-(3-hydroxyprop-1-ynyl)phenyl]methyl}carboxamide (0.23 g, 0.82 mmol) (Step B) and NMO (0.14 g, 1.3 mmol) was added catalytic amount of TPAP. The resulting mixture was stirred for 1 h at RT, then filtered over a short pad of SiO2 and concentrated. To a solution of the residue and morpholine (0.1 mL, 1.2 mmol) in CH2Cl2 was added excess NaBH(OAc)3. The resulting solution was stirred for 16 h, diluted with CH2Cl2 and saturated aq. NaHCO3 solution. The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by SiO2 chromatography to give a colorless oil, which was dissolved in 5 mL of CH2Cl2. To the organic solution was added TFA (2 mL). The resulting solution was stirred for 1 h at RT, then concentrated. The residue was diluted with CH2Cl2 and saturated aq. NaHCO3 solution. The organic layer was separated, dried over Na2SO4, and concentrated to give the title compound. MS (ES+): 249 (M+H)+; (ES−): 247. Calc'd C14H17FN2O-248.30.

1. filtrationfiltered over a short pad of SiO2
2. concentrationconcentrated
3. stirringThe resulting solution was stirred for 16 h
4. customThe organic layer was separated
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. customThe residue was purified by SiO2 chromatography
8. customto give a colorless oil, which
9. stirringThe resulting solution was stirred for 1 h at RT
10. concentrationconcentrated
11. additionThe residue was diluted with CH2Cl2 and saturated aq. NaHCO3 solution
12. customThe organic layer was separated
13. dry with materialdried over Na2SO4
14. concentrationconcentrated