Hydrochloric Acid → [6-Fluoro-4-(piperidin-4-yloxy)-naphthalen-2-yl]-acetic acid methyl ester

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Reaction Steps

To a solution of 4-(7-fluoro-3-methoxycarbonylmethyl-naphthalen-1-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (prepared as described above, 400 mg, 0.99 mmol) in methanol (4 mL) was added a 5N solution of hydrogen chloride in methanol (4 mL). After being stirred at room temperature for 3 hours, the mixture was concentrated in vacuo. The residue was dissolved in dichloromethane (10 mL), and treated with a saturated aqueous sodium bicarbonate solution (10 mL). The aqueous layer was separated and extracted with dichloromethane (10 mL×2). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (elution with 10% methanol in dichloromethane) to afford [6-fluoro-4-(piperidin-4-yloxy)-naphthalen-2-yl]-acetic acid methyl ester (260 mg, 85%) as a pale yellow solid.

Provenance & Evidence