Methyl morpholine oxide → HCID 9829637, compound

HRID 2288556Notes

Reaction equation

HRID 2288556 reaction equation
[Br:1][C:2]1([Br:28])[CH2:4][CH:3]1[C:5]1[C:6]([CH:22]([OH:27])[C:23]([F:26])([F:25])[F:24])=[N:7][N:8]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:12][C:11]=2[Cl:21])[CH:9]=1.C[N+]1([O-])CCOCC1>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Br:28][C:2]1([Br:1])[CH2:4][CH:3]1[C:5]1[C:6]([C:22](=[O:27])[C:23]([F:24])([F:26])[F:25])=[N:7][N:8]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([C:17]([F:20])([F:18])[F:19])=[CH:12][C:11]=2[Cl:21])[CH:9]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 9959882HCID 9959882, compound

Product 1

HCID 9829637HCID 9829637, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

Tetra-n-propylammonium perruthenate (50 mg) was added to a stirred solution of the title compound of Example 2 (0.15 g) and 4-methylmorpholine N-oxide (50 mg) in acetonitrile (5 ml) containing powdered 4 Å molecular sieves. The reaction mixture was stirred at room temperature for 24 hours and then evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel, using dichloromethane as eluant, followed by chromatographic reprocessing, using hexane and then a mixture of hexane: ethyl acetate (19:1) as eluants, gave the title compound as a colourless oil. δ (CDCl3): 1.83 (t,1H), 2.20 (dd,1H), 3.24 (dd,1H), 7.44 (s,1H), 7.79 (s,2H). IR (thin film): νmax 1722.9 cm-1.

Workup

  1. additioncontaining
  2. customevaporated under reduced pressure
  3. customPurification of the residue by column chromatography on silica gel
  4. additiona mixture of hexane: ethyl acetate (19:1) as eluants

Sources & evidence

ORD record
ord-6f3104258d714fc88f93a920b89a2fc8
Source dataset
uspto-grants-2000_07
Patent number
US06090394

Reaction notes

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