[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:6]([CH:9]=1)[CH:7]=O.Cl.[CH2:17]([NH2:19])[CH3:18].C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>CO.C(O)(=O)C>[CH2:17]([NH:19][CH2:7][C:6]1[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:10][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:18]
5-Chloro-2-cyclopentoxybenzaldehyde (9.35 g, 41.6 mmol) and ethylamine hydrochloride (18.6 g, 229 mmol) in methanol (100 ml) for 30 minutes at ambient temperatures, following which sodium cyanoborohydride (5.6 g, 88 mmol) was added and the reaction left to reflux at 70° C. for 70 hours with periodic acidification to pH 6 using glacial acetic acid. Normal hydrochloric acid (100 ml) was added in a dropwise fashion and the resultant mixture basified with 2 normal sodium hydroxide solution until a pH of 11 existed, whereupon the product was extracted into dichloromethane (250 ml×2) and ethyl acetate (250 ml×2). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered and the solvent removed to yield the title compound (8.5 g, 80%).
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