Sodium Sulfite → HCID 69075646, compound

HRID 1785278Notes

Reaction equation

HRID 1785278 reaction equation
[F:1][C:2]1([F:33])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:32])([C:24]2[CH:29]=[CH:28][C:27]([CH:30]=C)=[CH:26][CH:25]=2)[C:8]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[O:9])[CH2:3]1.S([O-])([O-])=[O:35].[Na+].[Na+]>O1CCCC1.O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[F:1][C:2]1([F:33])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:32])([C:24]2[CH:25]=[CH:26][C:27]([CH2:30][OH:35])=[CH:28][CH:29]=2)[C:8]([O:10][CH:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH2:15][CH2:16]2)=[O:9])[CH2:3]1

Participants

6

Reactant 2

HCID 24437Sodium SulfiteHCID 69073653HCID 69073653, compound

Product 1

HCID 69075646HCID 69075646, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolvent2×HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 69 mg of the t-butyl 4-((2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-vinylphenyl)ethanoyloxy)-tetrahydropyridine-1(2H)-carboxylate as obtained in Referential Example 56 in 2 ml of tetrahydrofuran-water (1:1), 85 mg of sodium periodide and 0.1 ml of 2% osmium tetraoxide were added at 0° C., followed by an hour's stirring at the same temperature. Adding sodium sulfite to the reaction liquid, stirring was continued for further 30 minutes. The reaction liquid was 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 was dissolved in 1 ml of methanol. To the solution 10 mg of sodium borohydride was added, stirred for 10 minutes and acetone was added. The reaction liquid was 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 resulting residue was purified on preparative thin layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), hexane/ethyl acetate=1/1) to provide 42 mg of the title compound as a colorless oily substance.

Workup

  1. waitfollowed by an hour
  2. stirringstirring
  3. customThe reaction liquid
  4. washwashed successively with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationDistilling the solvent off under reduced pressure
  7. dissolutionthe residue was dissolved in 1 ml of methanol
  8. additionTo the solution 10 mg of sodium borohydride was added
  9. stirringstirred for 10 minutes
  10. additionacetone was added
  11. customThe reaction liquid
  12. washwashed successively with water and saturated brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. distillationDistilling the solvent off under reduced pressure
  15. customthe resulting residue was purified on preparative thin layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-44ea4f623b554ee5b9186fbc14c5ea0e
Source dataset
uspto-grants-2009_03
Patent number
US07504432B2

Reaction notes

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