[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[N:15]1C=CC=CC=1.B.Cl.[CH3:23][OH:24]>>[CH3:23][O:24][NH:15][CH2:13][CH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=1A mixture of 3-(4-acetamidophenyl)propanal (96 mg, 0.50 mmol), methoxy]amine hydrochloride (92 mg, 1.1 mmol), and pyridine (110 μL) in methanol (0.7 mL) is heated in a 70° C. oil bath for 18 hours and then allowed to cool to room temperature. Methanol (1 mL) is added and the mixture is cooled to 0° C. in an ice-water bath. Borane.pyridine complex (0.11 mL, 1.1 mmol) is added, followed by the dropwise addition of 10% aqueous hydrochloric acid. The mixture is allowed to warm to room temperature and then concentrated under reduced pressure. The residue is purified by reverse-phase HPLC to give N-[4-(3-methoxyamino-propyl)-phenyl]-acetamide.
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