Water → 2-(4-tert-Butylphenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid

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To a solution of dimethyl 2-(4-tert-butylphenyl)piperidine-1,4-dicarboxylate (10.937 g, 32.80 mmol) in MeCN (100 mL) was added lithium bromide (6.58 mL, 262.42 mmol), triethylamine (18.19 mL, 131.21 mmol) and water (2 mL). The resulting mixture was heated under reflux for 3 h, then cooled to room temperature. The solvents were evaporated and the residue dissolved in water. The aqueous layer was washed with MTBE, then acidified by the addition of 3.8 N HCl. The aqueous layer was extracted three times with DCM. The combined organic layers were dried over MgSO4 and evaporated. 2-(4-tert-Butylphenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (9.5 g, 91%) was isolated as a light brown foam. MS m/z 320 (M+H)+

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