Water → HCID 59633941, compound

HRID 1615078Notes

Reaction equation

HRID 1615078 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=1)[CH:2]=[CH2:3].[OH2:15].C[N+]1([O-])CC[O:20]CC1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(#N)C.[Os](=O)(=O)(=O)=O>[OH:15][CH:2]([CH2:3][OH:20])[CH2:1][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 59633949HCID 59633949, compound2×

Product 1

HCID 59633941HCID 59633941, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a mixed solution of ethyl 4-allylpyridin-2-carboxylate (0.28 g) prepared in (1) in acetonitrile (9.0 mL)/water (3.0 mL) were added 4-methylmorpholine N-oxide (0.34 g) and aqueous 4% osmium tetraoxide (0.40 mL). The reaction mixture was stirred at RT for 12 hr. An excess amount of saturated aqueous Na2S2O3 was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over Na2SO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: ethyl acetate/methanol=10/1) to give the title compound (0.25 g, 77%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customThe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel chromatography (Developing solvent: ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-0b56a794fab940c6b790fa0e4feafebe
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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