Dimethyl Sulfate → 1-Benzyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate

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Ozone was passed through a solution of 1-benzyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate (10.0 g, 0.0315 mol) in methylene chloride (200.0 mL) at −78° C. until the color of the solution turned to steel blue. The reaction mixture was flushed with an atmosphere of nitrogen. Then to the solution was added dimethyl sulfate (6.0 mL, 0.063 mol) followed by triethylamine (8.8 mL, 0.063 mol). The mixture was stirred at room temperature for overnight, and then concentrated. The residue was dissolved in ethyl acetate, and the resulting solution was washed with saturated NH4Cl solution, NaHCO3 (7.5%), brine, dried over Na2SO4, filtered and concentrated to give 1-benzyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate.

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