Reaktion #1913646

Reaktionsgleichung

1-hexyl-1H-pyrrole-2,5-dione

1-(3-Pyridinyl)-1-ethanone hydrazone

potassium hydroxide

→

ammonia

title compound

Ausbeute 29.5%

3-Hexyl-6-methyl-6-(3-pyridinyl)-3-azabicyclo[3.1.0]hexane-2.4-dione

Ausbeute 29.5%

Lösungsmittel

ethanol

dioxan

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through a pad of Celite®
2. 2
   Temperaturthe reaction mixture was heated to 90° C. for 7 h
3. 3
   Temperaturcooled to room temperature for 16 h
4. 4
   TemperaturThe reaction mixture was heated
5. 5
   Temperaturunder reflux for 16 h
6. 6
   workup.STIRRINGstirred at room temperature for 72 h
7. 7
   Einengenbefore concentrating in vacuo
8. 8
   SonstigeThe reaction mixture was purified by chromatography
9. 9
   Wascheneluting with dichloromethane

Vorschrift

1-(3-Pyridinyl)-1-ethanone hydrazone (Preparation 76, 0.69 g, 5.3 mmol) was dissolved in dioxan (30 ml) and manganese dioxide (0.85 g, 5.3 mmol) was added portionwise followed by a saturated solution of potassium hydroxide in ethanol (0.5 ml). The reaction mixture was stirred at room temperature for 1.5 h and then filtered through a pad of Celite®. To half of the filtrate was added 1-hexyl-1H-pyrrole-2,5-dione (Preparation 56, 0.48 g, 2.6 mmol) and the reaction mixture was heated to 90° C. for 7 h and then cooled to room temperature for 16 h. The reaction mixture was heated under reflux for 16 h and then stirred at room temperature for 72 h before concentrating in vacuo. The reaction mixture was purified by chromatography using silica gel (30 g) eluting with dichloromethane:0.880 ammonia (99:1) and then dichloromethane:methanol:0.880 ammonia (97:2:1) to afford the title compound (0.22 g, 29%).

Quelle