Tetrabutylammonium Fluoride → HCID 68502126, compound

Participants

Reaction Steps

A solution of 0.225 g of tert-butyl 3-[4,4-dimethyl-2-oxo-1-(2-trimethylsilanylethoxymethyl)-1,2,3,4-tetrahydroquinolin-8-ylmethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 2.5 ml of tetrahydrofuran is admixed with 2.5 ml of tetrabutylammonium fluoride solution (1M in tetrahydrofuran) and stirred at reflux over 6.5 hours. The reaction mixture is cooled to room temperature, poured onto water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.40 (1:1 EtOAc-heptane); Rt=5.97.

Provenance & Evidence