Reaktion #44046

Reaktionsgleichung

tert-Butyl 1-piperazine carboxylate

cesium carbonate

2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

2-methyl-5-quinolinyl trifluoromethanesulfonate

2-Methyl-5-quinolinyl trifluoromethanesulfonate

→

title compound

Ausbeute 62.0%

1,1-Dimethylethyl 4-(2-methyl-5-quinolinyl)-1-piperazinecarboxylate

Ausbeute 62.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux under nitrogen for 8 hours
2. 2
   SonstigeThe reaction was quenched at room temperature
3. 3
   Extraktionextracted into ethyl acetate (3×20 mL)
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe crude was purified by flash chromatography
7. 7
   Wascheneluting with ethyl acetate/cyclohexane (3/7)

Vorschrift

tert-Butyl 1-piperazine carboxylate (1.6 g; 1.2 eq), cesium carbonate (1.7 g; 1.5 eq), palladium acetate (0.33 g; 0.14 eq) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.97 mg; 0.15 eq) were added to a solution of 2-methyl-5-quinolinyl trifluoromethanesulfonate (D1) in toluene (20 mL) under an inert atmosphere. The reaction mixture was stirred at reflux under nitrogen for 8 hours. The reaction was quenched at room temperature using a saturated aqueous solution of ammonium chloride (15 mL) and extracted into ethyl acetate (3×20 mL). The organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by flash chromatography, eluting with ethyl acetate/cyclohexane (3/7) affording the title compound in 62% yield (1.4 g).

Quelle