Tetrabutylammonium Fluoride → Ethyl 4-[[6-(4-hydroxy-1-piperidyl)-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoate

Participants

Reaction Steps

To a solution of ethyl 4-[[6-[4-(tert-butyl(dimethyl)silyl)oxy-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoate (342 mg, 0.650 mmol) in THF (4 ml) is added Bu4NF 1.0 M in THF (0.975 ml, 0.975 mmol) at 0° C. The reaction mixture is gradually warmed to ambient temperature. After 12 hours, the reaction mixture is diluted with ice-water and extracted with ethyl acetate. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by flash chromatography (silica gel) over a gradient using 0-40% ethyl acetate in hexanes to afford the title compound (223 mg, 83.3%). Mass spectrum (m/z): 412.2 (M+1).

Provenance & Evidence