Methyl morpholine oxide → HCID 86657761, compound

HRID 1630757Notes

Reaction equation

HRID 1630757 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6](=[O:18])[N:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:8]=1.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:7]2[C:6](=[O:18])[CH:5]=[CH:4][C:3]([CH:2]=[O:1])=[CH:8]2)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 67416359HCID 67416359, compound

Product 1

HCID 86657761HCID 86657761, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-hydroxymethyl-1-(4-methoxy-benzyl)-1H-pyridin-2-one (35 mg, 151.5 μmol, 1 eq), 4-methyl morpholine N-oxide (26.7 mg, 227.2 μmol, 1.5 eq) and powdered 4 Å molecular sieves in dichloromethane (10 mL) was added in one portion tetrapropylammonium perruthenate (2.7 mg, 7.5 μmol, 0.05 eq). The reaction was stirred at rt for 2 h. After this time, the mixture was filtered through silica and the silica plug was washed with 95:5 dichloromethane/methanol. The filtrates were combined and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 2:1 ethyl acetate/hexane to give 1-(4-methoxy-benzyl)-6-oxo-1,6-dihydro-pyridine-3-carbaldehyde. Mass Spec. m/z=230 [M+H+].

Workup

  1. filtrationAfter this time, the mixture was filtered through silica
  2. washthe silica plug was washed with 95:5 dichloromethane/methanol
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography
  5. washeluting with 2:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-f6d7a694a3bb4e7aba7bd3550b05629e
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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