Sodium Sulfite → (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 0.85 g of potassium permanganate in 25 cm3 of water and 120 cm3 of acetone was added over approximately 1 hour, with stirring and at a temperature in the region of 25° C., to a solution of 1.2 g of (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetaldehyde in 60 cm3 of acetone. The mixture was stirred for 3 hours at this same temperature and then cooled to approximately 10° C. A solution of 5 g of sodium sulfite in 200 cm3 of water was added to the reaction mixture and then the mixture obtained was filtered through celite. The acetone of the filtrate was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. and then the evaporation residue was taken up in 200 cm3 of water and washed with 200 cm3 of diethyl ether. The aqueous phase was separated by settling, acidified with citric acid in the solid state to a pH in the region of 3-4 and extracted with 200 cm3 of diethyl ether. The ethereal solution, separated by settling, was dried over magnesium sulfate, filtered, and evaporated under the above conditions. 0.74 g of (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetic acid was obtained in the form of a yellow solid.

Provenance & Evidence