[ClH:1].[CH2:2]([CH:5]1[NH:11][C:10](=[NH:12])[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH:3]=C.[BH4-].[Na+].C([OH:17])C.O.Cl>C(Cl)Cl.CO.O.C(O)(=O)C>[ClH:1].[NH:12]=[C:10]1[NH:11][CH:5]([CH2:2][CH2:3][OH:17])[CH2:6][CH2:7][CH2:8][CH2:9]1Hexahydro-7-(2-propenyl)-1H-azepin-2-imine, monohydrochloride (the product of EXAMPLE 108) (3.0 g, 14.7 mmol) is dissolved in a mixture of methylene chloride (100 mL) and methanol (50 mL) and cooled to -78° C. Ozone is then bubbled through until a blue color is observed. The reaction is flushed with N2 to remove excess ozone. The reaction mixture is warmed to room temperature and concentrated in vacuo to a residue. The residue is dissolved in ethanol (100 mL), cooled to 0° C., and vigorously stirred as a cold solution of sodium borohydride (0.7 g, 18.5 mmol) in 1:1 ethanol-water is added. The pH of the reaction mixture is maintained by the concomitant addition of 2M acetic acid in water, maintaining the pH (pH paper) at 8 to 9. After the addition is complete, the mixture is stirred at room temperature for 10 hr, the reaction mixture is acidified to pH 2 with dilute HCl, and the reaction mixture is concentrated in vacuo to a gum. The gum is dissolved in a small amount of ethanol, filtered, evaporated in vacuo to a solid, dissolved in water and applied to an ion exchange column of Dowex 50 (H+). The column is washed with deionized water, and the title compound eluted with 2N HCl. The eluate is concentrated in vacuo to a solid, dissolved in a small amount of water, filtered, and lyophilized to give the title compound. C8H16N2O.HCl mw=192.69
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