Water ethylacetate → (4R)-4-(2-bromo-4-chlorophenyl)pyrrolidin-2-one
Reaktionsgleichung
N[C:2]1[CH:3]=[C:4]([C@@H:10]2[CH2:14][NH:13][C:12](=[O:15])[CH2:11]2)[C:5]([Br:9])=[CH:6][C:7]=1[Cl:8].C(OCC)(=O)C.O.N([O-])=O.[Na+]>S(=O)(=O)(O)O>[Br:9][C:5]1[CH:6]=[C:7]([Cl:8])[CH:2]=[CH:3][C:4]=1[C@@H:10]1[CH2:14][NH:13][C:12](=[O:15])[CH2:11]1Komponenten
Reaktionsbedingungen
- Temperatur
- 55 °C
Versuchsvorschrift
(4R)-4-(3-Amino-6-bromo-4-chlorophenyl)pyrrolidin-2-one was dissolved in 32 mL of sulfuric acid aqueous solution (1M) and the heated at 55° C. for 20 min. The reaction mixture was cooled to 0° C. and 160 mL ethyl acetate/water added. To this mixture, 1.5 equivalent of NaNO2 was added portion wise. The reaction was monitored by LCMS. After the starting material was consumed, the mixture was diluted with water and extracted with dichloromethane. The combined organic phases were washed with water and brine, and dried over sodium sulfate. The solvent was removed to provide the title compound as an off-white solid (4.7 g, 55% yield). 1H-NMR (400 MHz, CD3OD): δ 2.38-2.44 (dd, J=17.2, 4.0 Hz, 1H), 2.73-2.80 (dd, J=17.2, 9.2 Hz, 1H), 3.33-3.37 (dd, J=10.0, 6 Hz, 5.6 Hz, 1H), 3.78-3.83 (dd, J=10.0, 8.0 Hz, 1H), 4.06-4.13 (m, 1H), 7.64-7.65 (m, 1H), 7.38 (m, 2H); MS (ESI) m/z 275.89 (M+H)+.
Aufarbeitung
- temperatureThe reaction mixture was cooled to 0° C.
- customAfter the starting material was consumed
- additionthe mixture was diluted with water
- extractionextracted with dichloromethane
- washThe combined organic phases were washed with water and brine
- dry with materialdried over sodium sulfate
- customThe solvent was removed
Quellen und Nachweise
- ORD-Eintrag
- ord-3f739c79cc3d4340879203e37a9bddfb
- Quelldatensatz
- uspto-grants-2013_01
- Patentnummer
- US08344028B2
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