Triethylamine → HCID 66732094, compound

Participants

Reaction Steps

Dimethyl 2-(4-(methylsulfonyl)benzyl)piperidine-1,4-dicarboxylate (5.5 g, 14.89 mmol) was dissolved in acetonitrile (50 mL) and water (1 mL), then lithium bromide (10.34 g, 119.10 mmol) and triethylamine (8.25 mL, 59.55 mmol) were added and the resulting suspension was heated at reflux for 2 h. Water and MTBE were added. The organic phase was extracted with water (×2). To the pooled aqueous layer was added ethyl acetate and the solution was acidified to pH 1 with HCl and then extracted with ethyl acetate twice. The organic layer was dried (Na2SO4), filtered through celite and evaporated to yield 1-(methoxycarbonyl)-2-(4-(methylsulfonyl)benzyl)piperidine-4-carboxylic acid (4.2 g, 79%). MS m/z 354 (M−H)−

Provenance & Evidence