p-Toluenesulfonic acid → 3-cyano-N-[2-(4-fluoro-2-methylphenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide

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Reaction Steps

3-Cyano-N-[2-(4-fluoro-2-methylphenyl)-4-(tetrahydro-2H-pyran-2-yloxy)butyl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide (460 mg, 0.96 mmol) was dissolved in methanol (10 mL) together with 4-toluenesulfonic acid (37 mg, 0.2 mmol) and the solution was stirred at room temperature overnight. An aqueous solution of NaHCO3 together with CH2Cl2 was added and the organic solution was then washed with brine, dried and the solvent removed by evaporation. There was obtained 350 mg (92%) of 3-cyano-N-[2-(4-fluoro-2-methylphenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide as an oil. 1H NMR (300 MHz, CDCl3): 1.0-2.3 (cm, 6H), 2.4 (s, 3H), 2.6 (s, 3H), 2.7-4.5 (cm, 10H), 6.4-7.4 (cm, 5H).

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