Water → HCID 22163834, compound

Participants

Reaction Conditions

Reaction Steps

Tetrabutylammonium fluoride (11.5 g) is added in small portions at a temperature in the region of 0° C. to a solution of 3-(5-tert-butyldimethylsilyloxy-2-oxopentyl)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone (9.2 g) in anhydrous tetrahydrofuran (185 cc), and the solution obtained is stirred for 5 minutes at a temperature in the region of 0° C. The reaction mixture is then stirred for 1 hour 30 minutes at a temperature in the region of 20° C. and then poured into a mixture of ice (200 g) and water (600 cc). The insoluble product is separated by filtration, washed successively with water (5×25 cc) and diisopropyl ether (2×10 cc) and dried in the air. After recrystallization in acetonitrile, 3-(5-hydroxy-2-oxopentyl)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone (5.6 g), m.p. 152° C., is obtained.

Provenance & Evidence