OO.[OH:3][N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]([OH:12])[CH2:6][C:5]1([CH3:14])[CH3:13].[CH2:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.CO>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2].CS(O)(=O)=O>[CH:15]1([O:3][N:4]2[C:9]([CH3:10])([CH3:11])[CH2:8][CH:7]([OH:12])[CH2:6][C:5]2([CH3:14])[CH3:13])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1A solution of 80.2 g (1.18 mol) of 50% aqueous hydrogen peroxide is added at 70° C. over 12 hours to a mixture of 17.2 g (100 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-ol, 0.556 g (2.00 mmol) of iron(II) sulfate heptahydrate, 0.679 g (2.0 mmol) of tetrabutylammonium hydrogen sulfate, 0.15 ml (2.0 mmol) of methanesulfonic acid, 44 ml of cyclohexane, and 200 ml of methanol. Five hours after the peroxide addition is started, a solution of 0.556 g (2.0 mmol) of iron(II) sulfate heptahydrate and 0.15 ml (2.0 mmol) of methanesulfonic acid in 4 ml of water is added to the reaction mixture. Shortly after the peroxide addition is completed, the reaction mixture tests negative for hydrogen peroxide. Methanol is distilled from the reaction mixture at reduced pressure, and water and saturated sodium bicarbonate solution are added to the reaction mixture. A total of 60 ml of 12% by weight sodium borohydride in 14 N sodium hydroxide solution is added to the reaction mixture to convert any 4-oxo derivative of the title compound to the desired product. The reaction mixture is extracted with dichloromethane, and the organic layer is neutralized by the addition of hydrochloric acid followed by sodium bicarbonate. After drying, the organic layer is concentrated, and the crude product is purified by flash chromatography on silica gel to afford 15.0 g (59% yield) of the title compound, an off white solid having a melting point of 72-75° C. Structure is confirmed by mass spectrometry and NMR analysis.
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