Triacetoxyperiodinane → tert-Butyl 4-formylpiperidine-1-carboxylate

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Reaction Steps

A Dess-Martin reagent (7.89 g) was added to a solution of tert-butyl 4-hydroxymethylpiperidine-1-carboxylate (4.00 g) in dichloromethane (40 ml), and the mixture was stirred for 1.5 hours at room temperature. After diluting with ethyl acetate, the reaction solution was washed with a 1% aqueous solution of sodium hydroxide and a brine successively. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1) to yield tert-butyl 4-formylpiperidine-1-carboxylate (2.43 g) as a colorless oil.

Provenance & Evidence