Methanol → 3-Hexyl-6-(3-nitrophenyl)-6-propyl-3-azabicyclo[3.1.0]hexane-2,4-dione

Temperature

10 °C

1-(3-Nitrophenyl)-1-butanone hydrazone (Preparation 63, 1.0 g, 4.8 mmol) was dissolved in dioxan (20 ml) and cooled to 10° C., manganese dioxide (grade CMD-1 from Sumitomo, 10 g, 117 mmol) was added portionwise. After the addition was complete, the reaction mixture was stirred at room temperature for 30 minutes. This suspension was filtered over a pad of Celite® directly into a solution of 1-hexyl-1H-pyrrole-2,5-dione (Preparation 56, 0.88 g, 4.5 mmol) in dioxan (20 ml). The Celite® pad was washed with dioxan (125 ml) and then stirred at room temperature for 20 h. The reaction mixture was concentrated in vacuo to give a crude orange oil. Methanol (8 ml) was added and the mixture was cooled to 0° C. and upon scratching a white solid precipitated. The solid was filtered off and washed with cold methanol to give the pure product, the mother liquors were concentrated in vacuo and treated again with methanol under the procedure described above to give further product. The title compound was obtained as a white solid (0.28 g, 16%).

1. additionAfter the addition
2. washThe Celite® pad was washed with dioxan (125 ml)
3. stirringstirred at room temperature for 20 h
4. concentrationThe reaction mixture was concentrated in vacuo
5. customto give a crude orange oil
6. temperaturethe mixture was cooled to 0° C.
7. customprecipitated
8. filtrationThe solid was filtered off
9. washwashed with cold methanol
10. customto give the pure product
11. concentrationthe mother liquors were concentrated in vacuo
12. additiontreated again with methanol under the procedure
13. customto give further product

ORD record

ord-7ff74d31cd2d45848bb0af473f9e5399

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313312B1