4-(Hydroxy-quinolin-2-yl-methyl)-4-propyl-piperidine-1-carboxylic acid tert-butyl ester → 4-Propyl-4-(quinoline-2-carbonyl)-piperidine-1-carboxylic acid tert-butyl ester

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To a solution of 4-(hydroxy-quinolin-2-yl-methyl)-4-propyl-piperidine-1-carboxylic acid tert-butyl ester (190 mg, 0.5 mmol) in toluene (5 mL) was added manganese (IV) oxide (activated, 260 mg, 3.0 mmol). The reaction mixture was heated at 100° C. for 3 hours, then cooled to room temperature and filtered through Celite, rinsing with EtOAc. The filtrate was concentrated and purified by flash chromatography (0% to 20% EtOAc in hexanes) to provide 124 mg (67%) of 4-propyl-4-(quinoline-2-carbonyl)-piperidine-1-carboxylic acid tert-butyl ester as a colorless oil.

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