Reaktion #611072

Reaktionsgleichung

EtOAc

NaH

di-pyridin-2-yl-amine

methyl 6-bromohexanoate

→

II

Ausbeute 24.0%

6-(Di-pyridin-2-yl-amino)-hexanoic acid methyl ester

Ausbeute 24.0%

Lösungsmittel

Brine

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe phases were separated
2. 2
   Extraktionthe aqueous phase was extracted with EtOAc (100 mL)
3. 3
   Trocknendried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigesubsequently evaporated under reduced pressure
6. 6
   SonstigeThe resulting residue was purified by silica gel column chromatography

Vorschrift

NaH (112 mg, 2.92 mmol) was added to di-pyridin-2-yl-amine (500 mg, 2.92 mmol) in DMF (10 mL) at rt. After 10 min, KI (485 mg, 2.92 mmol) and methyl 6-bromohexanoate, I (0.464 mL, 2.92 mmol) were added, and the reaction mixture was stirred at 90° C. for 21 h. Brine (200 mL) and EtOAc (200 mL) were then added, the phases were separated, and the aqueous phase was extracted with EtOAc (100 mL). The organic phases were combined, dried over MgSO4, filtered, and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using CH2Cl2/MeOH (100:0.5 to 100:1) as eluant to furnish II as a colourless oil (206 mg, 24%).

Quelle