Tetrabutylammonium Fluoride → Methyl 3-[[2-(4-hydroxy-1-piperidyl)quinoline-4-carbonyl]amino]-2,4-dimethyl-benzoate

Participants

Reaction Steps

To a solution of methyl 3-(2-(4-((tert-butyldimethylsilyl)oxy)piperidin-1-yl)quinoline-4-carboxamido)-2,4-dimethylbenzoate (1.30 g, 0.00087 mol) in THF (2.0 ml) is added Bu4NF 1.0 M in THF (10.0 ml) at 0° C. The reaction mixture is gradually warmed to ambient temperature. After 14 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) with ethyl acetate in hexanes to afford the title compound as a yellow solid (0.10 g, 27%). Mass spectrum (m/z): 434.3 (M+1).

Provenance & Evidence