Triethylamine → HCID 66731923, compound

Participants

Reaction Steps

Dimethyl 2-(3,5-di-tert-butylbenzyl)piperidine-1,4-dicarboxylate (3.886 g, 9.63 mmol) was dissolved in acetonitrile (40 mL) and water (0.8 mL), then lithium bromide (6.69 g, 77.04 mmol) and triethylamine (5.34 mL, 38.52 mmol) were added and the resulting yellow suspension was heated at reflux. After 5 h water (100 mL) and MTBE (250 mL) were added. The organic phase was extracted with water (×2). The pooled aqueous layer was acidified to pH 1 with 3.8 M HCl and then extracted with MTBE (×3). The combined organic layer was washed with water, dried Na2SO4, filtered and evaporated to yield 2-(3,5-di-tert-butylbenzyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (3.723 g, 99%) as a yellow gum. MS m/z 390 (M+H)+

Provenance & Evidence