Hydrogen Peroxide → HCID 73159784, compound

HRID 1073975Notes

Reaction equation

HRID 1073975 reaction equation
[C:1]([N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]([NH:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:6][C:5]1([CH3:18])[CH3:17])(=[O:3])[CH3:2].C[OH:20].O.OO>[O-][W]([O-])(=O)=O.[Na+].[Na+].C(OCC)(=O)C>[CH2:14]([CH:13]=[N+:12]([CH:7]1[CH2:6][C:5]([CH3:17])([CH3:18])[N:4]([C:1](=[O:3])[CH3:2])[C:9]([CH3:10])([CH3:11])[CH2:8]1)[O-:20])[CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 962WaterHCID 54222474HCID 54222474, compound

Product 1

HCID 73159784HCID 73159784, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 12.4 g (48.6 mmol) of 1-acetyl-4-n-butylamino-2,2,6,6-tetramethylpiperidine, 0.8 g (2.4 mmol) of sodium tungstate, 85 ml of methanol and 20 ml of water at 0° C. is added 19.9 ml (195 mmol) of 30% aqueous hydrogen peroxide. After stirring for one hour at 0° C., the reaction mixture is allowed to warm to room temperature and is stirred for an additional 2.5 hours. Ethyl acetate is added and the organic phase is then washed with water, and brine, dried over anhydrous sodium sulfate and concentrated. The crude product is purified by flash chromatography on silica gel (12:2:1, ethyl acetate:hexane: methanol) to yield 4.8 g (37%) of the title compound as a clear oil.

Workup

  1. temperatureto warm to room temperature
  2. stirringis stirred for an additional 2.5 hours
  3. washthe organic phase is then washed with water, and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product is purified by flash chromatography on silica gel (12:2:1, ethyl acetate:hexane: methanol)

Sources & evidence

ORD record
ord-6ade6162194842c9b82e89228e81b213
Source dataset
uspto-grants-1990_11
Patent number
US04972009

Reaction notes

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