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

Participants

Reaction Conditions

Reaction Steps

A suspension of 2.45 g of methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate, 2.1 g of potassium carbonate, 0.95 g of potassium iodide, and 0.6 cm3 of propargyl bromide in 50 cm3 of acetonitrile was stirred for 40 hours at a temperature in the region of 20° C. in an inert atmosphere. After filtering the reaction mass, the filtrate was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained was purified by chromatography on a column of silica gel (particle size 20-45 μm; diameter 2.5 cm; mass 50 g), elution was carried out with ethyl acetate, and 60-cm3 fractions were collected. Fractions 6 to 12 were combined and then concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 1.35 g of methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-(prop-2-ynyl)piperidine-3-carboxylate were obtained in the form of a gum.

Provenance & Evidence