Water → Tert-butyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-4-hydroxymethylpiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

1.05 g of lithium aluminum hydride was added portionwise, with stirring and under an inert atmosphere, to a solution of 12.3 g of ethyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate in 250 cm3 of tetrahydrofuran, at a temperature in the region of −20° C. After stirring for 2 hours at a temperature in the region of 20° C., 0.5 g of lithium aluminum hydride was added to the reaction mixture at a temperature in the region of −20° C. After 1 and a half hours, the reaction mixture was cooled to 0° C. and was then hydrolyzed by successive addition of 1.8 cm3 of water, 1.3 cm3 of 5N sodium hydroxide and 5.7 cm3 of water. After stirring for 30 minutes at a temperature in the region of 20° C., the reaction mixture was filtered and then washed with 400 cm3 of ethyl acetate. The filtrate was washed with 200 cm3 of saturated sodium chloride solution, dried over magnesium sulfate and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 10.9 g of tert-butyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-4-hydroxymethylpiperidine-1-carboxylate were obtained.

Provenance & Evidence