[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11].Cl.OO.N=O.[CH2:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>O.O=[Fe].O=[Fe]O[Fe]=O.C(#N)C>[CH:18]1([O:1][N:2]2[C:7]([CH3:8])([CH3:9])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]2([CH3:12])[CH3:11])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1Iron (II,III) oxide (0.107 g, 0.462 mmol) is added to a mixture of 2.51 g (14.6 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-ol, 24 ml of acetonitrile, and 15 ml of cyclohexane. The reaction mixture is brought to reflux, and a solution of 0.306 g of concentrated hydrochloric acid in 2 ml of water is added. A solution of 4.49 g (66 mmol) of 50% aqueous hydrogen peroxide is added dropwise over 70 minutes to the reaction mixture while the reaction temperature is maintained at 60-62 degrees. After approximately 65% of the peroxide is added, 0.055 g (0.238 mmol) of iron (II,III) oxide and a solution of 0.107 g of concentrated hydrochloric acid are added to the reaction mixture. The mixture is heated at reflux after the peroxide is added until GC analysis shows that the starting nitroxyl compound is no longer present. After work up and purification according to the procedure of Example 54, the yield of the title compound is 1.87 g (50% yield), GC assay 96%.
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