[C:1]([CH:5]1[CH2:16][CH2:15][C:8]2([O:12][CH2:11][CH:10]([CH2:13][NH2:14])[CH2:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C:17]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[C:1]([CH:5]1[CH2:16][CH2:15][C:8]2([O:12][CH2:11][CH:10]([CH2:13][NH:14][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]To a solution of 8-t-butyl-3-aminomethyl-1-oxaspiro(4,5)-decane (1.2 g, 5.3 mmol), cyclohexanone (0.54 g, 5.5 mmol) and zinc chloride (0.4 g, 3 mmol) in methanol (15 ml) was added sodium cyanoborohydride (0.4 g, 6.4 mmol). The reaction mixture was stirred over night. The solvent was then evaporated in vacuo and the resulting residue was treated with a mixture of saturated aqueous sodium carbonate/toluene (50 ml each). The organic layer was separated, dried (MgSO4) and evaporated in vacuo to yield 1.7 g of a pale yellow oil which was purified by flash chromatography (toluene/ethanol 4:1). Evaporation of the fractions containing the product yielded a colourless oil (1.5 g).
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