1,2-Dichloroethane → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-acetoxyethylsulfonyl)acetamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

72 μl of methanesulfonic acid were added to a solution of 0.47 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. The resulting mixture was cooled to -10° C. 0.51 g of 3-chloroperoxybenzoic acid (purity: was added to the reaction mixture, which was then stirred at a temperature in the range from -10° C. to -5° C. for 2 hours. At the end of this time, the reaction mixture 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, and then the solvent was removed by distillation under reduced pressure. The 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 0.40 g (yield 40%) of the title compound as an oil.

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