Reaktion #45390

Reaktionsgleichung

sodium borohydride

Ethyl magnesium bromide

pyridine nitrile

THF

methanol

→

1-(6-Bromo-pyridin-2-yl)-propylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature over 1 hr
2. 2
   Sonstigebefore quenching with saturated ammonium chloride solution (10 mL)
3. 3
   workup.ADDITIONThe mixture was diluted with water (20 mL)
4. 4
   Extraktionextracted with ethyl acetate (3×30 mL)
5. 5
   TrocknenThe combined organics were dried (MgSO4)
6. 6
   Sonstigeevaporated in vacuo
7. 7
   Sonstigepurified by column chromatography
8. 8
   Sonstigeto yield A466.3 (237 mg)
9. 9
   Sonstige4.6×33 mm (2 min grad)

Vorschrift

Ethyl magnesium bromide (3.0 mL, 3.0 mmol) was added dropwise over 10 min to a solution of the pyridine nitrile A466.2 (500 mg, 2.75 mmol) in THF (5 mL) at room temperature under a nitrogen atmosphere. After strring for 30 min at room temperature, the reaction mixture was then cooled to 0° C. and anhydrous methanol added (2.75 mL) followed by sodium borohydride (15 mg, 3.0 mmol). The mixture was allowed to warm to room temperature over 1 hr before quenching with saturated ammonium chloride solution (10 mL) and stirring overnight at room temperature. The mixture was diluted with water (20 mL) and extracted with ethyl acetate (3×30 mL). The combined organics were dried (MgSO4), evaporated in vacuo and purified by column chromatography using 10% MeOH in ethyl acetate as eluant to yield A466.3 (237 mg). HPLC YMC S-5 4.6×33 mm (2 min grad): retention time 0.87 min, M+H+=217.15

Quelle