Réaction #43656

Équation de réaction

HCl

Nitromethane

2-((3-Pyridinyl)methylene)-1-azabicyclo[2.2.2]octan-3-one

sodium methoxide

→

oil

Rendement 64.0%

2-(1-(3-Pyridinyl)-2-nitroethyl)-1-azabicyclo[2.2.2]octan-3-one

Rendement 64.0%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was heated
2. 2
   Températureat reflux for 3 h
3. 3
   ConcentrationThe mixture was concentrated by rotary evaporation
4. 4
   Autreto yield a solid brown residue
5. 5
   AutreThe residue was purified by column chromatography

Mode opératoire

2-((3-Pyridinyl)methylene)-1-azabicyclo[2.2.2]octan-3-one (6.4 g, 0.024 mol) in dry methanol (45 mL) was added drop-wise to sodium methoxide (produced in situ, 0.036 mol). Nitromethane (3.7 mL, 0.068 mol) was then added, and the mixture was heated at reflux for 3 h. After cooling to room temperature, 1 N HCl was slowly added to adjust pH to 8. The mixture was concentrated by rotary evaporation to yield a solid brown residue. The residue was purified by column chromatography, using ethyl acetate/hexane (1:1, v/v), followed by chloroform/methanol/ammonia (90:10:1, v/v), as eluent, to obtain a yellow oil (4.2 g, 64%).

Source