Sodium Chloride → HCID 86757666, Verbindung
Reaktionsgleichung
O1CC[CH2:4][CH2:3][CH:2]1O[N:8]1[C@@H:11](C)[C@@H:10](C/C=C/[Sn](CCCC)(CCCC)CCCC)[C:9]1=[O:29].[Cl:30][C:31]1[CH:36]=[CH:35][C:34](I)=[CH:33][CH:32]=1.[OH-].[NH4+].[Cl-].[Na+]>CN(C)C=O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:30][C:31]1[CH:36]=[CH:35][C:34](/[CH:2]=[CH:3]/[CH3:4])=[CH:33][CH:32]=1.[CH3:31][N:8]1[CH2:11][CH2:10][C:9]1=[O:29]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution of (3R,4S)-1-(2-tetrahydropyranyloxy)-3-((2E)-3-tributylstannyl-2-propene-1-yl)-4-methylazetidin-2-one (0.92 g, 1.79 mmol) in 3 mL of dimethylformamide is added 4-chloroiodobenzene (470 mg, 1.97 mmol) and triphenyphosphine palladium (II) dichloride (63 mg, 0.09 mmol). The resulting solution is heated at 80° C. for 16 h, then 0.5 mL ammonium hydroxide is added. The reaction mixture is poured into saturated sodium chloride solution (20 mL) and extracted with 1:1 EtOAc-hexane (50 mL). The combined organic layers were dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography (elution with 3:1 hexanes-EtOAc) to provide (3R,4S)-1-(2-tetrahydropyranyloxy)-3-((2E)-3-(4-chlorophenyl)-2-propene-1-methylazetidin-2-one as an oil (370 mg, 61% yield).
Aufarbeitung
- extractionextracted with 1:1 EtOAc-hexane (50 mL)
- dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- custompurified by silica gel chromatography (elution with 3:1 hexanes-EtOAc)
Quellen und Nachweise
- ORD-Eintrag
- ord-7c7f9eb55e844d67b39191ddf37d38c9
- Quelldatensatz
- uspto-grants-2001_12
- Patentnummer
- US06329400B1
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