Reacción #72943

Ecuación de reacción

potassium hydroxide

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

methylamine

sodium cyanoborohydride

→

amine

Rendimiento 83.0%

3-Aminomethyl-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octane

Rendimiento 83.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture stirred at room temperature for 48 h
2. 2
   Otrothe solvent was removed by rotary evaporation
3. 3
   ExtracciónThe residue was extracted with chloroform (3×50 mL)
4. 4
   Secadodried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated by rotary evaporation

Procedimiento

2-((3-Pyridinyl)methyl)-1-azabicyclo[2.2.2]octan-3-one (2.16 g, 0.01 mol), methylamine (25 mL, 0.05 mol) and zinc chloride (5 mL, 0.005 mol) were added to dry methanol (30 mL) and stirred at room temperature for 30 min. Then, sodium cyanoborohydride (30 mL, 1.0M in THF) was added carefully and the mixture stirred at room temperature for 48 h. The mixture was adjusted to pH 10 using 2N potassium hydroxide and then the solvent was removed by rotary evaporation. The residue was extracted with chloroform (3×50 mL), dried (MgSO4), filtered and concentrated by rotary evaporation to yield the crude desired amine as a light yellow oil (2.40 g, 83% yield). The product was taken on to the next step without further purification.

Fuente