Hydroxyamine hydrochloride → 4-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one oxime

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Reaction Steps

To a solution of 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (0.125 g, 0.4 mmol) in pyridine (2 mL) was added hydroxylamine hydrochloride (0.031 g, 0.44 mmol), the mixture was stirred at room temperature under an argon atmosphere for 4 h and the solvent was evaporated. The mixture was partitioned between water and ethyl acetate, was extracted twice with ethyl acetate, the organic extract was dried (potassium carbonate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 25% ethyl acetate/hexanes, followed by trituration of the product with ether/hexanes provided a white solid (0.125 g, 95%): m.p. 50°-53° C. Analysis Calc. for C19H24N2O3 : C 69.44, H 7.37, N 8.53; found: C 69.35, H 7.47, N 8.28.

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