Methanol → HCID 131724015, compound

Participants

Reaction Steps

A solution of 1.26 g of (3RS,4RS)-4-[3-(R,S)-hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-carboxylic acid in 50-cm3 of methanol was cooled to a temperature in the region of −25° C. with stirring and under an inert atmosphere. 1.6-cm3 of thionyl chloride were added to this solution over 25 minutes. The mixture was brought to a temperature in the region of 20° C., while the stirring was continued for a further 48 hours. The reaction mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C., taken up in 100-cm3 of toluene and the mixture was again concentrated under reduced pressure (5 kPa). The residue was taken up in 50-cm3 of diisopropyl ether, triturated and concentrated to dryness under reduced pressure (5 kPa). 1.17 g of methyl (3RS,4RS)-4-[3-(R,S)-hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate dihydrochloride were obtained in the form of a yellow powder.

Provenance & Evidence