[CH2:1]([C:4](=[N:11][NH:12]C(OC(C)(C)C)=O)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:2][CH3:3].C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>C1COCC1.CO>[CH2:1]([CH:4]([NH:11][NH2:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:2][CH3:3]39.41 g (145.7 mmol) of tert-butyl N′-(1-propyl-heptylidene)-hydrazinecarboxylate are dissolved in a mixture of 100 ml of THF and 150 ml of methanol and, after 10.65 g (169 mmol) of sodium cyanoborohydride have been added, the mixture is stirred for 1 hour at room temperature. 100 ml of 6N HCl are added dropwise in the course of 30 minutes and, after the addition has ended, the mixture is refluxed for 1 hour. The mixture is neutralized with 6N NaOH solution, then, after the non-aqueous solvents have been removed, extracted three times with dichloromethane, and, after the mixture has been dried over sodium sulphate, the solvent is removed in vacuo. This gives 23.90 g (95%) of a yellow oil.
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