Methyl morpholine oxide → HCID 53235480, compound

HRID 1506311Notes

Reaction equation

HRID 1506311 reaction equation
[CH3:1][C:2]1([CH3:32])[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH:30]=C)[CH:28]=2)[C:5]2=[N:6][O:7][C:8]([C:9]3[O:13][N:12]=[C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:10]=3[C:20]([F:23])([F:22])[F:21])=[C:4]2[CH2:3]1.C[N+]1([O-])CC[O:37]CC1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[CH3:32][C:2]1([CH3:1])[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH:30]=[O:37])[CH:28]=2)[C:5]2=[N:6][O:7][C:8]([C:9]3[O:13][N:12]=[C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:10]=3[C:20]([F:21])([F:23])[F:22])=[C:4]2[CH2:3]1

Participants

8

Reactant 3

HCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 67171970HCID 67171970, compound

Product 1

HCID 53235480HCID 53235480, compoundYield 94%

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5,5-dimethyl-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 1E, 0.036 g, 0.082 mmol) and NMO in water (0.017 mL, 0.082 mmol) in THF (1.5 mL) at room temperature was added osmium tetroxide in water (0.013 mL, 1.65 μmol). The reaction mixture was stirred at room temperature for 7 hours. A solution of sodium periodate (0.026 g, 0.124 mmol) in water (1 mL) was added via syringe. The resulting cloudy reaction mixture was stirred overnight at room temperature concentrated under reduced pressure, and the residue was diluted with ethyl acetate (30 mL) and washed with water (15 mL). The organic layer was washed with brine and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded 5,5-dimethyl-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde (0.034 g, 0.078 mmol, 94% yield) as a tan solid. The product had an HPLC ret. time=3.51 min. (condition A); LC/MS M+1=439.1.

Workup

  1. customThe resulting cloudy reaction mixture
  2. stirringwas stirred overnight at room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate (30 mL)
  5. washwashed with water (15 mL)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-7a514676ddee471389fe07f4b304abe0
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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