Réaction #77883

Équation de réaction

spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

nitric acid

sodium carbonate

→

title compound

Rendement 51.0%

5′-Nitrospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

Rendement 51.0%

Solvants

sulfuric acid

Conditions de réaction

Traitement

1. 1
   Températurewas heated at 70° C. to 80° C. for 24 hours
2. 2
   ExtractionThe resulting mixture was extracted with chloroform (4×15 mL)
3. 3
   Séchagedried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated under reduced pressure
6. 6
   AutrePurification by flash chromatography through silica gel
7. 7
   Lavageeluting with ammoniated chloroform/methanol (95:5)

Mode opératoire

A mixture of spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]′ (325 mg, 1.5 mmol) and fuming nitric acid (0.27 mL, 5.74 mmol) in sulfuric acid (0.75 mL) was heated at 70° C. to 80° C. for 24 hours. The resulting viscous solution was poured onto 15 g of ice and basified to pH>10 with solid sodium carbonate. The resulting mixture was extracted with chloroform (4×15 mL), dried (MgSO4), filtered, and evaporated under reduced pressure. Purification by flash chromatography through silica gel, eluting with ammoniated chloroform/methanol (95:5), provided the title compound (200 mg, 0.765 mmol, 51%) as a light yellow solid: electrospray MS 262 ([MH]+, 100).

Source