Potassium Iodide → 1-[1-(4-Fluorophenyl)-2-hydroxy-2-quinolin-8-ylethyl]pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

0.615 ml (5.18 mmol) of 4-chlorobutyryl chloride (95%) was slowly added dropwise to a solution of 1.5 g (4.7 mmol) of 2-amino-2-(4-fluorophenyl)-1-quinolin-8-ylethanol hydrochloride and 1.96 ml (14.1 mmol) of triethylamine in 15 ml of DMF cooled to −8° C. After stirring at −8 to −10° C. for 1 h, 2.25 g (56.3 mmol) of sodium hydroxide pellets and 156 mg (0.94 mmol) of potassium iodide were added, and the mixture was stirred at room temperature for 3 h. The mixture was poured into an aqueous sodium dihydrogen phosphate solution (80 g/l). Extraction twice with diisopropyl ether was followed by drying over magnesium sulfate. The residue after concentration in vacuo was purified by chromatography with petroleum benzene/ethyl acetate 50:50, then 30:70 to 0:100. 845 mg of 1-[1-(4-fluorophenyl)-2-hydroxy-2-quinolin-8-ylethyl]pyrrolidin-2-one (diastereoisomer A) (yield: 51%) and 127 mg of 1-[1-(4-fluorophenyl)-2-hydroxy-2-quinolin-8-ylethyl]pyrrolidin-2-one (diastereomer B) (yield: 8%) were obtained.

Provenance & Evidence