Potassium Iodide → methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(5-chlorothien-2-yl)ethyl]piperidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 1 g of methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate in 40 cm3 of acetonitrile and 10 cm3 of methanol was stirred at a temperature. in the region of 20° C. and then 1.16 g of potassium carbonate and 0.5 g of potassium iodide were added. 1 g of 2-chloro-5-(2-chloroethylthio)thiophene and 10 cm3 of acetonitrile were added to the suspension obtained. The mixture was stirred for 72 hours at a temperature in the region of 80° C. The reaction mass was poured onto 75 cm3 of ethyl acetate and then washed with 3 times 70 cm3 of water. The organic phase was dried over sodium sulfate, filtered, and evaporated under reduced pressure (5 kPa) at a temperature in the region of 45° C. The residue obtained was purified by chromatography under a nitrogen pressure of 40 kPa on a column of silica gel (particle size 20-40 μm; diameter 3.5 cm; silica height 31 cm), elution was carried out with ethyl acetate, and 30-cm3 fractions were collected. Fractions 24 to 52 were combined and concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 0.48 g of methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(5-chlorothien-2-yl)ethyl]piperidine-3-carboxylate was obtained in the form of an oil with a brown color.

Provenance & Evidence