반응 #2124615

반응 방정식

6-allyl-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one

THF H2O

→

3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one

용매

EtOAc

반응 조건

후처리

1. 1
   건조dried over Na2SO4
2. 2
   농축concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in MeOH (10 mL)
4. 4
   workup.ADDITIONNaBH4 (0.200 g) was added
5. 5
   workup.STIRRINGAfter the mixture was stirred for 1 h at rt
6. 6
   workup.ADDITIONacetone was added
7. 7
   기타The solvents were removed in vacuo
8. 8
   workup.ADDITIONthe residue was treated with saturated brine
9. 9
   추출extracted with CH2Cl2
10. 10
    건조dried over Na2SO4
11. 11
    기타After the solvents were evaporated
12. 12
    기타the residue was purified by chromatography on silica gel
13. 13
    세척eluted with hexanes/EtOAc

실험 절차

To a solution of 6-allyl-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (obtained as described in Example 111) in THF-H2O (1:1, 20 mL) were added NaIO4 (1.0148 g, 4.74 mmol, 5 equiv) and OsO4 (2.5 wt. % solution in t-BuOH, 0.1708 g, 0.0167 mmol, 0.018 equiv), and the mixture was stirred at rt for 2 h. The mixture was diluted with EtOAc, dried over Na2SO4, and concentrated under reduced pressure. The residue was dissolved in MeOH (10 mL) and NaBH4 (0.200 g) was added. After the mixture was stirred for 1 h at rt, acetone was added. The solvents were removed in vacuo, the residue was treated with saturated brine, extracted with CH2Cl2, and dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford the two diastereomers of 3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one.

출처