反应详情

A stock solution of H5IO6/CrO3 was prepared by dissolving H5IO6 (68.4 g, 0.3 mol) and CrO3 (138 mg, 1.2 mol %) in CH3CN (684 mL) to give a 0.44 M solution. To a solution of H5IO6/CrO3 (16 mmol, 36 mL, 0.44 M in THF) at −5° C. (ice and salt bath) was added a solution of (2S)-2-{[(1S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl]amino}-4-methylpentan-1-ol (1 g) in 3 mL THF dropwise. The internal temperature was monitored and reaction temperature was not allowed to rise above 0° C. The reaction was monitored by TLC until the reaction was complete (3-4 h). Na2HPO4 (80 mL) was added to the reaction mixture which was then extracted with EtOAc. The organic extract was washed with brine, NaHSO3 (120 mL) and brine again, dried over anhyd. MgSO4 and concentrated to an oil. The oil was redissolved in EtOAc and filtered through a short pad of silica gel, eluted with EtOAc and the filtrated was concentrated to give the title compound.

1. customreaction temperature
2. customto rise above 0° C
3. custom(3-4 h)
4. extractionwas then extracted with EtOAc
5. extractionThe organic extract
6. washwas washed with brine, NaHSO3 (120 mL) and brine again
7. customdried over anhyd
8. concentrationMgSO4 and concentrated to an oil
9. dissolutionThe oil was redissolved in EtOAc
10. filtrationfiltered through a short pad of silica gel
11. washeluted with EtOAc
12. concentrationthe filtrated was concentrated