Dimethyl Sulfoxide → 1-Methoxy-2,2,6,6-tetramethyl-piperidin-4-ol
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.C(=O)([O-])[O-].[Na+].[Na+]>Cl.C(Cl)Cl.[Cl-].[Ti+3].[Cl-].[Cl-]>[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
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 30 °C
Procedure
A solution of 7.2 g (5.6 mmol) of 12% titanium(III) chloride in hydrochloric acid is added dropwise under nitrogen over a 15 minute period to a mixture of 1.0 g (5.8 mmol) of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 1.0 g (8.8 mmol) of hydrogen peroxide, and 15 ml of dimethyl sulfoxide at a temperature of 20° C. The reaction temperature increases to 30° C. during the addition. The mixture is stirred for 45 minutes after the peroxide addition is complete, and is then diluted with methylene chloride (50 ml). The aqueous layer is neutralized by the addition of a saturated aqueous solution of sodium carbonate, then extracted with methylene chloride (50 ml). The combined organic layers are concentrated under reduced pressure, and the crude product is purified by flash chromatography on silica gel (4:1, heptane:ethyl acetate) to afford 100 mg (10% yield) of the title compound.
Workup
- extractionextracted with methylene chloride (50 ml)
- concentrationThe combined organic layers are concentrated under reduced pressure
- customthe crude product is purified by flash chromatography on silica gel (4:1, heptane:ethyl acetate)
Sources & evidence
- ORD record
- ord-d0132ef939a24a3f8578739fbfc334d5
- Source dataset
- uspto-grants-1994_12
- Patent number
- US05374729
Reaction notes
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