[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].S(=O)(=O)(O)O.O.OO.[CH2:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>[Cu].C(#N)C>[CH:21]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])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1Copper powder (0.060 g, 0.944 mmol) is added to a mixture of 5.00 g (29.0 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-ol, 44 ml of acetonitrile, and 30 ml of cyclohexane that has been heated to 40 degrees. A portion of a solution of 0.457 g of concentrated sulfuric acid in 3 mol of water is carefully added to the reaction mixture after the mixture is brought to reflux. To the refluxing reaction mixture is added dropwise over 2.5 hours a solution of 7.32 g (108 mmol) of 50% aqueous hydrogen peroxide. The remainder of the sulfuric acid solution is carefully added in portions to the reaction mixture during the first 15 minutes of the peroxide addition. After work up and purification according to the procedure of Example 54, the yield of the title compound is 5.22 g (70% yield), GC assay 94%.
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