Triethylamine → HCID 66732042, compound

Participants

Reaction Steps

To a solution of dimethyl 2-(4-(trifluoromethoxy)benzyl)piperidine-1,4-dicarboxylate (9.72 g, 25.90 mmol) in MeCN (80 mL) and water (1.6 mL) was added lithium bromide (18.2 g, 209.57 mmol) and triethylamine (15 mL, 108.21 mmol). The resulting mixture was heated under reflux for 3 h, then cooled to room temperature. Water and MTBE were added. The organic phase was extracted with water twice. The pooled aqueous layers were adjusted to pH 1 with 3.8 M HCl and then extracted with DCM (3×). The mixture was filtered through a diatomeous earth filter carton. The combined organic layers were dried over MgSO4 and evaporated. 1-(Methoxycarbonyl)-2-(4-(trifluoromethoxy)benzyl)piperidine-4-carboxylic acid (8.75 g, 94%) was isolated as a pale yellow solid. MS m/z 360 (M−H)−

Provenance & Evidence