Water → Octahydroisoindole

A solution of hexahydro-1H-isoindole-1,3(2H)-dione (1.0 g, 6.5 mmol) in dry THF (14 mL) was added dropwise to a stirred slurry of LiAlH4 in dry THF (6 mL) at such a rate that the solvent gentle refluxed. The resulting reaction mixture was heated to reflux for 20 h and then allowed to cool to RT. The reaction mixture was cooled with an ice-bath, and H2O (1 mL), a 20% aqueous solution of NaOH (2.5 mL) and H2O (2 mL) were sequentially added. The mixture was filtered and THF removed under reduced pressure. The aqueous phase was extracted with Et2O, and the separated organics were dried over Na2SO4, filtered and concentrated to dryness, affording the title compound (690 mg, 5.52 mmol) as a white powder that was used in the next step without any further purification.

1. customThe resulting reaction mixture
2. temperaturewas heated
3. temperatureto reflux for 20 h
4. temperatureThe reaction mixture was cooled with an ice-bath
5. filtrationThe mixture was filtered
6. customTHF removed under reduced pressure
7. extractionThe aqueous phase was extracted with Et2O
8. dry with materialthe separated organics were dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated to dryness

ORD 기록

ord-7f307cb0595d4e0bbb53530bab1043ed

출처 데이터셋

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08729098B2