Hydrochloric Acid → N-{4'-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-ylmethyl}-hydroxylamine

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Hydrochloric acid (4 N, in dioxane, 10 mL) was added dropwise into a mixture of 4′-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-carbaldehyde oxime (1.5 g, 3.56 mmol), sodium cyanoborohydride (1.1 g, 17.81 mmol), methyl alcohol (100 mL), and tetrahydrofuran (100 mL). The reaction mixture was stirred for 1 hour poured into water, basified with sodium hydroxide (2 N), and extracted with ethyl acetate. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on silica gel (EtOAc/MeOH 20:1) gave an off-white solid (1.21 g, 80% yield); MS m/e 424 (M+);

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