Cesium carbonate → Methyl 3-(4-benzyloxycarbonylaminopiperidin-1-yl)benzoate

HRID 43824

Reaktionsgleichung

Reaktionsgleichung von HRID 43824
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:64]1[CH2:69][CH2:68][CH:67]([NH:70][C:71](=[O:80])[O:72][CH2:73][C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)[CH2:66][CH2:65]1>O1CCOCC1.CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:73]([O:72][C:71]([NH:70][CH:67]1[CH2:68][CH2:69][N:64]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:65][CH2:66]1)=[O:80])[C:74]1[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=1

Komponenten

9

Edukt 4

HCID 10796Cesium carbonateHCID 12070Methyl 3-bromobenzoateHCID 634876Binap, (A+-)-HCID 15143044-Cbz-aminopiperidine

Produkt 1

HCID 68405998Methyl 3-(4-benzyloxycarbonylaminopiperidin-1-yl)benzoateAusbeute 26,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Methyl 3-bromobenzoate (230 mg, 1.07 mmol), palladium acetate (12 mg, 0.054 mmol), BINAP (133 mg, 0.214 mmol) and cesium carbonate (767 mg, 2.35 mmol) were added to a solution of benzyl piperidin-4-yl-carbamate obtained in Example (192b) (248 mg, 0.817 mmol) in 1,4-dioxane (10 mL) and N,N-dimethylformamide (2.5 mL), and the mixture was stirred at 100° C. for 20 hours. The reaction solution was cooled, diluted with ethyl acetate, and washed with brine. The organic layer was dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/1) to obtain 80 mg of the title compound as a colorless oily substance (20%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-2d442424469f4ef68a66b1df757b2b4d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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