Triethylamine → 2-(Cyclohexyloxymethyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid

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Reaction Steps

Dimethyl 2-(cyclohexyloxymethyl)piperidine-1,4-dicarboxylate (2.54 g, 8.1 mmol) was dissolved in acetonitrile (35 mL) and water (0.7 mL), then lithium bromide (5.63 g, 64.80 mmol) was added. Triethylamine (4.49 mL, 32.40 mmol) was added and the resulting suspension was heated under reflux for 4 h. MTBE (100 mL) and water (50 mL) were added, the phases separated and the organic layer was extracted with water. The combined aqueous layers were acidified to pH 1 with 3.8 M HCl and extracted with MTBE. The combined organic layers were dried with Na2SO4 and evaporated. 2-(Cyclohexyloxymethyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (2.43 g, quant.) was isolated. MS m/z 300 (M+H)+

Provenance & Evidence