Isobutyraldehyde → HCID 56948846, compound

Participants

Reaction Conditions

Reaction Steps

Lithiumchloride (4.2 mg, 0.1 mmol) which had been dried before in vacuum at 125° C. was placed in anhydrous acetonitrile (4 ml), the mixture was cooled to −78° C. and diethoxyphosphoryl-1-[1-(2-methyl-4-quinolyl)-4-piperidyl]ethanone from step B (40 mg, 0.1 mmol) dissolved in 1 ml anhydrous acetonitrile was added dropwise with stirring. The mixture was allowed to reach room temperature, stirring was continued for 10 minutes and diisopropylethylamine (10.1 mg, 0.1 mmol) and isobutyraldehyde (7.2 mg, 0.1 mmol) were added. Stirring was continued overnight. Water and dichloromethane (10 ml each) were added and the mixture poured into saturated ammoniumchloride solution (20 ml). The phases were separated, the aqueous phase extracted with dichloromethane (3×) and the combined organic phases washed with brine, dried over sodium sulfate and the solvent removed under reduced pressure. The raw product was purified with preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile). 9.5 mg of an amber-coloured solid were obtained (0.029 mmol, 29%).

Provenance & Evidence