[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[O:27]1[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28]1.[OH-].[Na+]>ClC(Cl)C>[CH2:1]([NH:8][CH2:32][C:29]1[CH:30]=[CH:31][O:27][CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Benzylamine (16 g, 150 mmol) was dissolved in dichloroethane (320 ml), and the solution was mixed with acetic acid (77 ml, 1.3 mol), sodium triacetoxyborohydride (57 g, 590 mmol) and 3-furaldehyde (13 g, 130 mmol) and stirred at room temperature for 16 hours. 5 N Sodium hydroxide aqueous solution was added to the reaction solution until it became basic, and the reaction product was extracted with ethyl acetate. The organic layer was washed with saturated brine and then dried with anhydrous magnesium sulfate. The solvent was removed by evaporation from the organic layer under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 19 g (100 mmol, 77% in yield) of the title compound.
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