Hydrochloric Acid → HCID 131723282, compound

Participants

Reaction Steps

1 drop of 5N aqueous sodium hydroxide solution and then, portionwise, 0.17 g of sodium borohydride were added, with stirring, to a solution, maintained at a temperature in the region of 20 ° C., of 0.84 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thienylthio)ethyl]piperidine-3-acetate in 12 cm3 of methanol. The mixture was stirred for 3 hours at a temperature in the region of 20° C. After adding 10 cm3 of water, the methanol was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained was extracted with 2 times 20 cm3 of dichloromethane and then the combined extracts were washed with 2 times 30 cm3 of water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. An oil was obtained, which oil was purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μm; diameter 2.5 cm; silica volume 150 cm3), elution was carried out with a dichloromethane/methanol (99/1 by volume) mixture. Fractions 56 to 115 were combined and then concentrated as above. An oil was obtained, the hydrochloride of which was prepared in the following way: the oil was dissolved in 20 cm3 of diethyl ether and then poured onto 2 cm3 of a 1 N solution of hydrochloric acid in ether. The precipitate formed was filtered off and dried in an oven under reduced pressure (10 Pa) at a temperature in the region of 40° C. 0.3 g of methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thienylthio)ethyl]piperidine-3-acetate dihydrochloride was obtained in the form of a white solid.

Provenance & Evidence