1-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine → tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylate

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Reaction Steps

A solution of 1-(tert-butoxycarbonyl)piperidine-4-ethanol (5.0 g, 22 mmol) in methylene chloride (100 mL) was treated with pyridinium chlorochromate (5.2 g, 24 mmol), and diatomaceous earth (5 g). After 3 days, the mixture was filtered through diatomaceous earth, concentrated, and the residue purified by column chromatography (SiO2: 20 to 30% EtOAc:hexanes) affording 4.0 g (81%) of the title compound.

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