Thionyl Chloride → HCID 69345641, compound

Participants

Reaction Steps

A solution of 940 mg of (3RS,4RS) and (3SR,4RS)-4-[3-(R,S)-hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetic acid in 20 cm3 of methanol was cooled to a temperature in the region of −25° C., with stirring and under an inert atmosphere. 0.43 cm3 of thionyl chloride were added to this solution over 5 minutes. The mixture was brought to a temperature in the region of 20° C. while the stirring was continued for a further 1 hour 30 minutes. The reaction mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. and then 30 cm3 of methanol were added. This series of operations was repeated 3 times. 920 mg of methyl (3RS,4RS) and (3SR,4RS)-4-[3-(R,S)-hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-3-acetate dihydrochloride were obtained in the form of a yellow foam.

Provenance & Evidence