Methanesulfonic Acid → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-acetoxyethylsulfinyl)acetamide

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Reaction Conditions

Reaction Steps

77 μl of methanesulfonic acid was added to a solution of 0.50 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-acetoxyethylthio)acetamide (prepared as described in Example 2) in 5.5 ml of 1,2-dichloroethane, and the resulting mixture was cooled to -10° C. 0.28 g of 3-chloroperoxybenzoic acid (purity: 80%) was then added, and the reaction mixture was stirred, whilst keeping the temperature in the range from -10° C. to -5° C., for 2 hours. At the end of this time, it was washed with a 10% w/v aqueous solution of sodium hydrogensulfite, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 1:9 by volume mixture of ethanol and chloroform as the eluent, to give 0.38 g (yield 73%) of the title compound as an oil.

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