Water → HCID 18346021, compound

HRID 1909680Notes

Reaction equation

HRID 1909680 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 68998776HCID 68998776, compound

Product 1

HCID 18346021HCID 18346021, compound

Reagents, catalysts & solvents 4

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

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-Hexahydro-[1,2,3]oxathiazolo[3,4-a]pyridine 1-oxide (1.31 g, 8.125 mmol) in anhydrous acetonitrile (10 mL) was added sodium (meta)periodate (1.91 g, 8.9375 mmol), followed by ruthenium(III) chloride hydrate (17 mg, 0.08125 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 DCM (80 mL). The combined organic layer was dried over Na2SO4, concentrated in vacuo, and purified by flash column chromatography (silica gel, 2% EtOAc in DCM) to afforded the title product as a clear, colorless oil (1.1 g, 76%).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (80 mL) and DCM (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 DCM)

Sources & evidence

ORD record
ord-0d765edc1a0e457fab266ae815921fb6
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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