Reaktion #651384

Reaktionsgleichung

1-[7-(2-chloro-acetyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoro-ethanone

4-benzyloxy-1H-pyridin-2-one

potassium tert-butylate

1-[7-(2-chloro-acetyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoro-ethanone

tert-butylammonium iodide

→

4-Benzyloxy-1-{2-oxo-2-[2-(2,2,2-trifluoro-acetyl)-1,2,3,4-tetrahydro-isoquinolin-7-yl]-ethyl}-1H-pyridin-2-one

Lösungsmittel

EtOAc

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe organic phase is washed with water
2. 2
   Filtrationfiltered
3. 3
   Trocknendried over MgSO4
4. 4
   Sonstigethe solvent is evaporated
5. 5
   SonstigeThe residue is purified via reverse HPLC chromatography (Zorbax stable bond; water (0.15% formic acid)/acetonitrile (0.15% formic acid) 95:5 to 5:95)

Vorschrift

To 600 mg (2.98 mmol) 4-benzyloxy-1H-pyridin-2-one in 6 mL THF is added at 0° C. 368 mg (3.28 mmol) potassium tert-butylate and 55 mg (0.15 mmol) tert-butylammonium iodide. After 5 min 1.00 g (3.28 mmol) 1-[7-(2-chloro-acetyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoro-ethanone is added. After 2 h additional 600 mg (1.97 mmol) 1-[7-(2-chloro-acetyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoro-ethanone is added and the mixture is stirred an additional hour. The reaction mixture is diluted with EtOAc and the organic phase is washed with water, filtered, dried over MgSO4 and the solvent is evaporated. The residue is purified via reverse HPLC chromatography (Zorbax stable bond; water (0.15% formic acid)/acetonitrile (0.15% formic acid) 95:5 to 5:95).

Quelle