Dimethyl Sulfoxide → 1-Methoxy-2,2,6,6-tetramethyl-piperidin-4-ol
Reaction equation
OO.[OH:3][CH:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[N:7]([OH:12])[C:6]([CH3:14])([CH3:13])[CH2:5]1.[CH3:15]S(C)=O>CCCCCCC.C(OCC)(=O)C>[CH3:15][O:12][N:7]1[C:8]([CH3:10])([CH3:11])[CH2:9][CH:4]([OH:3])[CH2:5][C:6]1([CH3:14])[CH3:13]Participants
Procedure
A solution of 9.1 g (80 mmol) of 30% aqueous hydrogen peroxide is added dropwise, under nitrogen, over a 30-minute period to a mixture of 10.0 g (58.1 mmol) of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 17.8 g (64.0 mmol) of ferrous sulfate heptahydrate, and 100 ml of dimethyl sulfoxide which is initially at 23° C. The reaction temperature reaches 65° C. during the addition. After the peroxide is all added, the reaction mixture is stirred for 30 minutes. During this time, the temperature falls to 35° C. The reaction mixture is partitioned between methylene chloride (150 ml) and water (100 ml). The organic layer is dried over anhydrous magnesium sulfate and concentrated at reduced pressure to obtain a yellow liquid. Purification by flash chromatography on silica gel (10:1 heptane/ethyl acetate, then 4:1 heptane/ethyl acetate) affords 6.5 g (60% yield) of the title compound.
Workup
- customis initially at 23° C
- additionThe reaction temperature reaches 65° C. during the addition
- customfalls to 35° C
- customThe reaction mixture is partitioned between methylene chloride (150 ml) and water (100 ml)
- dry with materialThe organic layer is dried over anhydrous magnesium sulfate
- concentrationconcentrated at reduced pressure
- customto obtain a yellow liquid
- customPurification by flash chromatography on silica gel (10:1 heptane/ethyl acetate
Sources & evidence
- ORD record
- ord-4f086a657bbf448e82ccc9f9d93b752d
- Source dataset
- uspto-grants-1994_12
- Patent number
- US05374729
Reaction notes
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