[CH2:1]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO.[Ni](Cl)Cl>[CH2:1]([CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=12.21 g of 3-benzylisoquinoline and 2.88 g of nickel dichloride.hexahydrate were dissolved in 50 mL of methanol at room temperature, and 4.58 g of sodium borohydride was added thereto over 30 minutes, followed by further stirring at room temperature for 4 hours. After completion of the reaction, water was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue obtained was purified using silica gel chromatography (chloroform:methanol=100:1→50:1) to obtain 1.85 g (yield 82%) of a title compound as a light yellow oily substance.
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