[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[CH3:10][O:11][C:12](=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=O)[CH:15]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CN1CCCC1=O>[CH3:10][O:11][C:12](=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[OH:1])[CH:15]=1A mixture of 2-hydroxybenzylamine (407 mg) and (3-formylphenyl)acetic acid methyl ester (594 mg) in dichloromethane (10 mL) and 1-methyl-2-pyrrolidone (10 mL) was treated with acetic acid (333 mg) followed by sodium triacetoxyborohydride (1.41 g) and the whole stirred at room temperature for 18 hours. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, the organic layer was washed twice with saturated aqueous brine before being separated, dried and evaporated under reduced pressure to yield the sub-titled compound (0.81 g).
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