Water → (1R,2S)-1'-(2-bromoethyl)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C@:10]3([C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][C:11]3=[O:19])[CH2:9]2)=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:30](Br)[CH2:31][Br:32].O>CN(C=O)C>[Br:32][CH2:31][CH2:30][N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@:10]2([CH2:9][C@H:8]2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:11]1=[O:19]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a solution of (1R,2S) and (1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one (173 mg, 0.64 m mol) in DMF (2 mL) was added KHMDS (0.5 M, 1.4 mL) dropwise at room temperature. The mixture was stirred for half an hour before adding ethylene dibromide (300 mg, 1.6 mmol). The mixture was warmed to 50° C. and stirred at that temperature for 14 hours. The mixture was poured into water, extracted with ethyl acetate (3×15 mL), dried and concentrated under reduced pressure. The residue was purified by flash column chromatography (gradient elution, 5-10% ethyl acetate in petroleum ether) to give the title compound as white solid (98 mg, 41%). LC/MS m/e calcd. for C18H15BrClNO: 375, observed (M+H)+: 376.
Aufarbeitung
- stirringstirred at that temperature for 14 hours
- extractionextracted with ethyl acetate (3×15 mL)
- customdried
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash column chromatography (gradient elution, 5-10% ethyl acetate in petroleum ether)
Quellen und Nachweise
- ORD-Eintrag
- ord-747f936876a84c258d7fb16c280ac833
- Quelldatensatz
- uspto-grants-2013_01
- Patentnummer
- US08354443B2
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