Reaktion #59361

Reaktionsgleichung

potassium hydroxide

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

methylamine

sodium cyanoborohydride

→

amine

Ausbeute 83.0%

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

Ausbeute 83.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred at room temperature for 48 h
2. 2
   Sonstigethe solvent was removed by rotary evaporation
3. 3
   ExtraktionThe residue was extracted with chloroform (3×50 mL)
4. 4
   Trocknendried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated by rotary evaporation

Vorschrift

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.

Quelle