3-[4-(4-Methanesulfonylpiperazin-1-yl)phenyl]-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester → 3-[4-(4-Methanesulfonylpiperazin-1-yl)phenyl]-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

HRID 40696

Reaktionsgleichung

Reaktionsgleichung von HRID 40696
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH:10]=[C:11]([C:16]1[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]3)=[CH:18][CH:17]=1)[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>COC(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH:9]2[CH2:15][CH2:14][CH:13]1[CH2:12][CH:11]([C:16]1[CH:21]=[CH:20][C:19]([N:22]3[CH2:23][CH2:24][N:25]([S:28]([CH3:31])(=[O:29])=[O:30])[CH2:26][CH2:27]3)=[CH:18][CH:17]=1)[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 674135093-[4-(4-Methanesulfonylpiperazin-1-yl)phenyl]-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 674120823-[4-(4-Methanesulfonylpiperazin-1-yl)phenyl]-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl esterAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 30156371-MethoxyethanolLösungsmittel

Versuchsvorschrift

3-[4-(4-Methanesulfonylpiperazin-1-yl)phenyl]-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester (0.83 g, 1.85 mmol) is solubilized in 93 ml of methoxyethanol. Palladium-on-carbon at 10% (0.395 g) is then added. The reaction medium is stirred for 5 h under 30 psi of hydrogen at 25° C. After filtration on Celite® and concentration, 0.76 g of expected 3-[4-(4-methanesulfonylpiperazin-1-yl)phenyl]-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester is obtained.

Aufarbeitung

  1. filtrationAfter filtration
  2. concentrationon Celite® and concentration

Quellen und Nachweise

ORD-Eintrag
ord-9fb0457a08a0492797d57db8b28d364a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530477B2

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