Triethylamine → HCID 66731611, compound

Participants

Reaction Steps

Dimethyl 2-((4,4-difluorocyclohexyl)methyl)piperidine-1,4-dicarboxylate (5.7 g, 17.10 mmol) was dissolved in acetonitrile (75 mL) and water (1.5 mL), then lithium bromide (11.88 g, 136.78 mmol) was added. Et3N (9.53 mL, 68.39 mmol) was added to the solution. The resulting yellow suspension was heated at reflux for 2 h. Water (100 mL) and MTBE (300 mL) were added. The phases were separated and the organic layer was extracted with water (2 times). The pooled water layers were acidified to pH 1 with 3.8 M HCl and extracted with MTBE (2 times). The combined organic layer was dried over Na2SO4, filtered and evaporated to yield 2-((4,4-difluorocyclohexyl)methyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (4.82 g, 88%) as a white solid.

Provenance & Evidence