Triethylamine → HCID 58270765, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-[amino(hydroxyimino)methyl]piperidine-1-carboxylate (3.0 g) in THF (30 mL) were added 3,5-difluorobenzoyl chloride (2.4 g) and triethylamine (3.44 mL) under ice-cooling, followed by stirring at room temperature for 2 hours. To the reaction liquid were added ethyl acetate and water, and the organic phase was separated. The organic phase was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To the residue were added THF (25 mL) and a 1 M tetrabutylammonium fluoride/THF solution (12.4 mL), followed by stirring at 50° C. for 30 minutes. The reaction liquid was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform). To the purified product was added diisopropyl ether, and the resulting solid was collected by filtration and dried to obtain tert-butyl 4-[5-(3,5-difluorophenyl)-1,2,4-oxadiazol-3-yl]piperidine-1-carboxylate (4.22 g) as an orange solid.

Provenance & Evidence