Potassium Carbonate → HCID 10783583, compound

Participants

Reaction Steps

To a degassed sample of 4-methylenepiperidine-1-carboxylic acid tert-butyl ester (0.527 g, 2.67 mmol) was added 9-borabicyclic[3,3,1]nonane (5.6 mL of a 0.5 M solution in THF, 2.8 mmol). The resulting solution was refluxed for 1 hour. After cooling to ambient temperature, the solution was added to a mixture of 1-iodo-2-trifluoromethylbenzene (0.707 mg, 2.600 mmol), Pd-catalyst (3 mol %), DMF (25 mL), water (1 mL), and K2CO3 (0.6 g). The resulting mixture was heated at 60° C. for 3 hours. The mixture was cooled to ambient temperature and then poured into water. The pH of the solution was adjusted to 11 with 10% NaOH solution and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4, filtered, and evaporated to give a crude oil, which was further purified by column chromatography to afford 4-(2-trifluoromethylbenzyl)piperidine-1-carboxylic acid tert-butyl ester as a waxy solid (0.638 g) in 70% yield.

Provenance & Evidence