Hydrochloric Acid → 5-Methyl-2,3-dihydro-1H-isoindole

Temperature

60 °C

The 4-methylphthalimide (1.8 g) obtained above was suspended in tetrahydrofuran (3 ml), then 1 N borane tetrahydrofuran complex (30 ml) was added thereto at room temperature and stirred overnight at 60° C. The mixture was cooled to 0° C., then methanol (2.8 ml) and 6 N hydrochloric acid (3.2 ml) were added thereto, and the mixture was refluxed for 1 hour. The reaction mixture was cooled to 0° C., then 6 N sodium hydroxide solution was added thereto, and the reaction solution was extracted with ethyl acetate and then the extract was dried over sodium sulfate anhydrous. The resulting product was concentrated under reduced pressure, and the residue was purified by column chromatography (eluting solvent; dichloromethane→dichloromethane:methanol 10:1→5:1) to give the title compound (400 mg, Y.:27%).

1. addition1 N borane tetrahydrofuran complex (30 ml) was added
2. temperatureThe mixture was cooled to 0° C.
3. temperaturethe mixture was refluxed for 1 hour
4. temperatureThe reaction mixture was cooled to 0° C.
5. extractionthe reaction solution was extracted with ethyl acetate
6. dry with materialthe extract was dried over sodium sulfate anhydrous
7. concentrationThe resulting product was concentrated under reduced pressure
8. customthe residue was purified by column chromatography (eluting solvent; dichloromethane→dichloromethane:methanol 10:1→5:1)

ORD record

ord-e43fd10ae3f1422aaad8f3618d8f308f

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07345180B2