Cesium carbonate → HCID 58547859, Verbindung

HRID 707341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 707341
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.Cl.[NH:19]1[CH2:22][CH:21]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:20]1>CN(C)C=O.O>[N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[N:19]1[CH2:22][CH:21]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:20]1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 119282-ChloroquinolineHCID 22101213tert-Butyl azetidin-3-ylcarbamate--hydrogen chloride (1/1)

Produkt 1

HCID 58547859HCID 58547859, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Cesium carbonate (4.68 g, 14.4 mmol), 2-chloroquinoline (0.782 g, 4.8 mmol) and tert-butyl azetidin-3-yl-carbamate hydrochloride (1.0 g, 4.8 mmol) were dissolved in dry dimethylformamide (15 mL) and the resulting mixture was heated at 120° C. overnight. The mixture was diluted with water (40 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water (30 mL) and brine (30 mL), then dried over sodium sulfate. The organic was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 40% ethyl acetate in petroleum ether) to give tert-butyl (1-(quinolin-2-yl)azetidin-3-yl)-carbamate (1.14 g, 3.84 mmol, 80% yield) as white solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined organic extracts were washed with water (30 mL) and brine (30 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe organic was evaporated in vacuo
  5. customthe residue was purified by flash column chromatography on silica gel (20% to 40% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-ef82a4e4f62c49918c68d410a37df44d
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174992B2

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