Ethyl 4-(hydroxymethyl)piperidine-1-carboxylate → Ethyl 4-formylpiperidine-1-carboxylate

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Reaction Steps

The above alcohol (7.5 g, 40.0 mmol, 1.0 equiv) was dissolved in 500 mL of CH2Cl2. Pyridinium chlorochromate (12.96 g, 60.1 mmol, 1.5 equiv) was added and resulting mixture was stirred for 16 h. The dark liquid was decanted and the solvent was removed in vacuo. The residue was triturated with 500 mL of diethyl ether and the mixture was filtered. The filtrate was washed with 150 mL of 1 N HCl and dried over Na2SO4. The liquid was decanted and concentrated by rotary evaporation to yield 4-formyl-piperidine-1-carboxylic acid ethyl ester as a light brown oil (6.1 g).

Provenance & Evidence