Thionyl Chloride → methyl (3R,4R)-1-tert-butyloxycarbonyl-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)-3-oxopropyl]piperidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

1.58 cm3 of a thionyl chloride solution are added, at a temperature in the region of 20° C., under an argon atmosphere, to 3.33 g (7.23 mmol) of (3R,4R)-1-tertbutyloxycarbonyl-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)-3-oxopropyl]piperidine-3-carboxylic acid in solution in 150 cm3 of dichloromethane. After stirring for 1 hour at a temperature in the region of 20° C., the reaction mixture is poured over a solution of 10.55 cm3 of N,N-diisopropylethylamine in 150 cm3 of methanol. After stirring for 16 hours at a temperature in the region of 20° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up with 150 cm3 of CH2Cl2, and washed with 3 times 50 cm3 of water and then 50 cm3 of a saturated aqueous sodium chloride solution. The organic phase is dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness under reduced pressure (2.7 kPa) to give 4 g of methyl (3R,4R)-1-tert-butyloxycarbonyl-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)-3-oxopropyl]piperidine-3-carboxylate in the form of an orange oil.

Provenance & Evidence