Sodium Hydroxide → HCID 69353351, compound

Participants

Reaction Conditions

Reaction Steps

3.9 cm3 of 1N aqueous sodium hydroxide were added to a solution of 0.6 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2ynyl]piperidine-3-carboxylate in 10 cm3 of dioxane and then the mixture was heated at a temperature in the region of 65° C. for 16 hours. The mixture was cooled and then the organic phase was extracted with 3 times 50 cm3 of ethyl acetate. The aqueous phase was acidified with 3.9 cm3 of 1N hydrochloric acid. The solution was taken up in 10 cm3 of a saturated aqueous sodium bicarbonate solution and then the organic phase was extracted with 2 times 20 cm3 of ethyl acetate and 2 times 20 cm3 of dichloromethane, dried over sodium sulfate, filtered, and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 45° C. 0.32 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperidine-3-carboxylic acid was obtained in the form of a foam with a white color.

Provenance & Evidence