Water → 1-(6-Chloro-5-trifluoromethylpyridin-2-yl)piperidin-4-yl-carbamic acid tert-butyl ester

HRID 490299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490299
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[C:18](Cl)[N:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.C(Cl)Cl>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:18]2[CH:19]=[CH:20][C:21]([C:22]([F:24])([F:25])[F:23])=[C:16]([Cl:15])[N:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 7238334-(N-Boc-amino)piperidineHCID 18103372,6-Dichloro-3-(trifluoromethyl)pyridine

Produkt 1

HCID 866126231-(6-Chloro-5-trifluoromethylpyridin-2-yl)piperidin-4-yl-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A stirred mixture of D7 (5.0 g, 25 mmol), 2,6-dichloro-3-trifluoromethyl-pyridine (5.4 g, 25 mmol) and cesium carbonate (12.22 g, 37.5 mmol) in 1,4-dioxane (75 mL) was heated at reflux under argon for 64 h. To the mixture, which was cooled to ambient temperature, was added water (250 mL) and DCM (250 mL) with shaking and the layers were separated. The aqueous phase was further extracted with DCM (250 mL) and the combined organic extracts were dried (MgSO4) and evaporated in vacuo to an oil. This material was purified by chromatography over silica gel eluting with a gradient of ethyl acetate/hexane to afford the title compounds

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux under argon for 64 h
  3. customthe layers were separated
  4. extractionThe aqueous phase was further extracted with DCM (250 mL)
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. customevaporated in vacuo to an oil
  7. customThis material was purified by chromatography over silica gel eluting with a gradient of ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-25b85cbeb7de498898bbe3ec1d392877
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528151B2

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