[Br:1][C:2]1[CH:3]=[C:4]([CH3:15])[C:5]([C:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH:9]=2)=[N:6][CH:7]=1.[NH2:16][CH2:17][CH2:18][OH:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH3:15])[C:5]([C:8]2[CH2:13][CH2:12][CH:11]([NH:16][CH2:17][CH2:18][OH:19])[CH2:10][CH:9]=2)=[N:6][CH:7]=1
To a solution of 4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-one (2.06 g) in dichloromethane (50 ml) was added 2-aminoethanol (0.463 ml) at room temperature with stirring. Then sodium triacetoxyborohydride (1.64 g) was added thereto, and stirred at the same temperature. After completion of the reaction, to the reaction solution was added 10% sodium carbonate aqueous solution, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with silica gel column chromatography (chloroform/methanol), and then suspended and washed with a mixed solvent of a small amount of diethyl ether and n-hexane to give 2-[4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]amino ethanol (860 mg) as a light brown solid.
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