Methyl morpholine oxide → HCID 54689900, compound

HRID 1244125Notes

Reaction equation

HRID 1244125 reaction equation
[OH:1][C:2]1[CH:3]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=3)=[CH:12][S:11][CH:4]2[NH:5][C:6](=[O:10])[C:7]=1[C:8]#[N:9].C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.ClCCl.CN(C)C(=O)C>[CH:20]([C:17]1[CH:18]=[CH:19][C:14]([C:13]2[CH:3]3[CH:4]([NH:5][C:6](=[O:10])[C:7]([C:8]#[N:9])=[C:2]3[OH:1])[S:11][CH:12]=2)=[CH:15][CH:16]=1)=[O:21]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 54689857HCID 54689857, compound

Product 1

HCID 54689900HCID 54689900, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 85741463dichloromethane N,N-dimethylacetamideSolvent

Procedure

Tetrapropylammonium perruthenate (0.16 g, 0.46 mmol) was added to a solution of 4-Hydroxy-3-(4-hydroxymethyl-phenyl)-6-oxo-3a,6,7,7a-tetrahydro-thieno[2,3-b]pyridine-5-carbonitrile (0.55 g, 1.84 mmol) and 4-methylmorpholine N-oxide (0.65 g, 5.52 mmol) in 2:1 mixture of dichloromethane/N,N-dimethylacetamide (33 mL) at room temperature. The reaction was stirred till complete consumption of the starting alcohol, filtered over celite, filtrate washed with 1N HCl, dried (MgSO4) and concentrated to a brown solid. MS (ESI) m/e 294.9 (M−H)+; 1H NMR (300 MHz, DMSO-d6): δ ppm 12.01 (br s, 1H), 10.04 (s, 1H), 7.87 (d, J=9, 2H), 7.66 (d, J=9, 2H), 7.07 (s, 1H).

Workup

  1. filtrationfiltered over celite, filtrate
  2. washwashed with 1N HCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to a brown solid

Sources & evidence

ORD record
ord-718c471c6a514d4691e715386d5f01a1
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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