Dimethyl Sulfoxide → 1-Methoxy-2,2,6,6-tetramethyl-piperidin-4-ol

HRID 1492702Notes

Reaction equation

HRID 1492702 reaction equation
[OH:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[N:5]([OH:10])[C:4]([CH3:12])([CH3:11])[CH2:3]1.OO.[CH3:15]S(C)=O.CCCCCCC.C(OCC)(=O)C>O>[CH3:15][O:10][N:5]1[C:6]([CH3:8])([CH3:9])[CH2:7][CH:2]([OH:1])[CH2:3][C:4]1([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 21899848Ethylacetate heptane

Product 1

HCID 109977701-Methoxy-2,2,6,6-tetramethyl-piperidin-4-olYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 17.8 g (64.0 mmol) of ferrous sulfate heptahydrate in 100 ml of water is added dropwise, under nitrogen, over an 8-minute interval to a mixture of 10.0 g (58.1 mmol) of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 14.5 g (128 mmol) of 30% aqueous hydrogen peroxide, and 200 ml of dimethyl sulfoxide. As the ferrous sulfate solution is added, an ice-water bath is used to keep the reaction temperature at 20° C.-40° C. After the addition is complete, the mixture is stirred for 15 minutes at ambient temperature and then extracted with methylene chloride (200 ml, then 100 ml). Purification of the crude product by flash chromatography on silica gel (10:1 heptane/ethyl acetate, then 4:1 heptane/ethyl acetate) affords 5.7 g (52% yield) of the title compound.

Workup

  1. customan ice-water bath is used
  2. customat 20° C.-40° C
  3. additionAfter the addition
  4. extractionextracted with methylene chloride (200 ml
  5. customPurification of the crude product by flash chromatography on silica gel (10:1 heptane/ethyl acetate

Sources & evidence

ORD record
ord-8854adef2555403cb0f3e8799a6ac6ad
Source dataset
uspto-grants-1994_12
Patent number
US05374729

Reaction notes

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