Oxolane--water (1/1) → HCID 66856810, compound

HRID 2037430Notes

Reaction equation

HRID 2037430 reaction equation
[CH2:1]([C:4]1([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=C.C1C[O:29]CC1.O>CCOC(C)=O.O=[Os](=O)(=O)=O>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:4]2([CH2:1][CH2:2][OH:29])[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH3:12])[CH2:6][CH2:5]2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 21881883Oxolane--water (1/1)HCID 59532357HCID 59532357, compound

Product 1

HCID 66856810HCID 66856810, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-allyl-6-(4-fluorophenyl)-3-((S)-1-phenylethyl)-1,3-oxazinan-2-one (0.1016 g, 0.30 mmol, 1.0 equiv) in THF-H2O (1:1, 6 mL) were added NaIO4 (0.3240 g, 1.5 mmol, 5 equiv) and OsO4 (2.5 wt. % solution in t-BuOH, 0.0507 g, 0.0049 mmol, 0.016 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 (3 mL) and NaBH4 (0.100 g) was added. After the mixture was stirred for 1.5 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 6-(4-fluorophenyl)-6-(2-hydroxyethyl)-3-((S)-1-phenylethyl)-1,3-oxazinan-2-one.

Workup

  1. dry with materialdried over Na2SO4
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in MeOH (3 mL)
  4. additionNaBH4 (0.100 g) was added
  5. stirringAfter the mixture was stirred for 1.5 h at rt
  6. additionacetone was added
  7. customThe solvents were removed in vacuo
  8. additionthe residue was treated with saturated brine
  9. extractionextracted with CH2Cl2
  10. dry with materialdried over Na2SO4
  11. customAfter the solvents were evaporated
  12. customthe residue was purified by chromatography on silica gel
  13. washeluted with hexanes/EtOAc

Sources & evidence

ORD record
ord-12fcd8340e414824b6c0d858a7b8dfcc
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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