Water → HCID 23255920, compound

HRID 749993Notes

Reaction equation

HRID 749993 reaction equation
[S@:1]1(=[O:10])[N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH:4]2[CH2:3][O:2]1.[O-:11]I(=O)(=O)=O.[Na+].O>C(#N)C.C([O-])(O)=O.[Na+].CCOC(C)=O.O.[Ru](Cl)(Cl)Cl>[S:1]1(=[O:11])(=[O:10])[N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C@@H:4]2[CH2:3][O:2]1

Participants

8

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 68998778HCID 68998778, compound

Product 1

HCID 23255920HCID 23255920, compound

Reagents, catalysts & solvents 4

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (R)-hexahydro-[1,2,3]oxathiazolo[3,4-a]pyridine 1-oxide (1.09 g, 6.76 mmol) in anhydrous acetonitrile (10 mL) was added sodium (meta)periodate (1.6 g, 7.436 mmol), followed by ruthenium(III) chloride hydrate (14 mg, 0.0676 mmol), and then H2O (10 mL). The mixture was stirred at 0° C. for 10 min and at rt for 20 min, then diluted with saturated NaHCO3 (30 mL) and EtOAc (100 mL). The aqueous layer was extracted with EtOAc (80 mL) and dichloromethane (80 mL). The combined organic layer was dried over Na2SO4, concentrated in vacuo, and purified by flash column chromatography (silica gel, 2% EtOAc in dichloromethane) to afforded the title product as a clear, colorless oil (0.890 g, 69%).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (80 mL) and dichloromethane (80 mL)
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash column chromatography (silica gel, 2% EtOAc in dichloromethane)

Sources & evidence

ORD record
ord-573bfab1e3d54a78a1aad802f4f396e6
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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