Sodium Sulfite → HCID 69081664, compound

HRID 458746Notes

Reaction equation

HRID 458746 reaction equation
C([O:4][C:5]1[CH2:9][C@H:8]([C@@:10]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14](=[O:15])[O:13][C@H:12]([C:16]([CH3:19])([CH3:18])[CH3:17])[O:11]2)[CH2:7][CH:6]=1)(=O)C.C[N+]1([O-])CC[O:30]CC1.S([O-])([O-])=O.[Na+].[Na+]>C(#N)C.O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[C:16]([C@H:12]1[O:13][C:14](=[O:15])[C@@:10]([C@H:8]2[CH2:7][C:6](=[O:30])[C@H:5]([OH:4])[CH2:9]2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[O:11]1)([CH3:17])([CH3:18])[CH3:19]

Participants

8

Reactant 3

HCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 69073113HCID 69073113, compound

Product 1

HCID 69081664HCID 69081664, compoundYield 20.5%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 169 mg of (4R)-4-((2R,4R)-2-(t-butyl)-5-oxo-4-phenyl-1,3-dioxolan-4-y)-1-cyclopentenyl acetate in 7.5 ml of acetonitrile and water (2:1), 80 mg of N-methyl morpholine-oxide and 0.2 ml of 2% aqueous osmium tetraoxide solution were successively added at 0° C. by the order stated, followed by 3 hours' stirring at the same temperature. Sodium sulfite was added to the reaction liquid and stirred for further 30 minutes. The reaction liquid was then diluted with ethyl acetate, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, the residue obtained was purified on silica gel column chromatography (eluent: hexane−hexane/ethyl acetate=2/1) to provide 32 mg of the title compound as a colorless solid.

Workup

  1. stirringstirred for further 30 minutes
  2. customThe reaction liquid
  3. washwashed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationDistilling the solvent off under reduced pressure
  6. customthe residue obtained
  7. customwas purified on silica gel column chromatography (eluent: hexane−hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-292a390b6c3a496fbaac4832427b5f0b
Source dataset
uspto-grants-2007_03
Patent number
US07192969B2

Reaction notes

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