(2-Methylsulfonylbenzyl)triphenylphosphonium chloride → 1-[(2-Methoxy-3-pyridyl)methyl]-4-[2-(methylsulfonyl)phenethyl]piperidine

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3.90 g of 1-[(2-methoxy-3-pyridyl)methyl]-4-piperidinecarboxaldehyde, 8.92 g of (2-methylsulfonylbenzyl)triphenylphosphonium chloride and 1.96 g of potassium tert-butoxide were suspended in 80 ml of N,N-dimethylformamide, and the mixture was stirred for 3 hours at room temperature. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by NH form silica gel column chromatography (ethyl acetate:hexane=1:4). The resulting product and 440 mg of 10% palladium-carbon powder (water-containing product) were suspended in 80 ml of ethanol. After replacing the atmosphere of a container with hydrogen, the mixture was stirred at room temperature under normal pressure for 30 minutes. The reaction solution was filtered, and the filtrate was evaporated, to give 4.05 g of the title compound as a colorless oil.

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