Acetic Acid → (5R)-5-{2-(4-chlorophenyl)-2-[6-methoxy-5-(1H-pyrazol-4-yl)pyridin-2-yl]ethyl}pyrrolidin-2-one

HRID 70693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 70693
C(O)(=O)C.[Cl:5][C:6]1[CH:11]=[CH:10][C:9](/[C:12](/[C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:27]=[N:28][NH:29][CH:30]=3)=[C:22]([O:31][CH3:32])[N:21]=2)=[CH:13]\[C@@H:14]2[NH:18][C:17](=[O:19])[CH2:16][CH2:15]2)=[CH:8][CH:7]=1.[H][H]>CO.[Pd]>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:30]=[N:29][NH:28][CH:27]=3)=[C:22]([O:31][CH3:32])[N:21]=2)[CH2:13][C@@H:14]2[NH:18][C:17](=[O:19])[CH2:16][CH2:15]2)=[CH:8][CH:7]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 67396156HCID 67396156, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 67397423(5R)-5-{2-(4-chlorophenyl)-2-[6-methoxy-5-(1H-pyrazol-4-yl)pyridin-2-yl]ethyl}pyrrolidin-2-oneAusbeute 62,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

10% palladium-activated carbon (60 mg) and acetic acid (2 mL) were added to a solution of (5R)-5-{(E)-2-(4-chlorophenyl)-2-[6-methoxy-5-(1H-pyrazol-4-yl)pyridin-2-yl]ethenyl}pyrrolidin-2-one (122 mg) in methanol (3 mL) in a hydrogen gas stream, and the mixture was stirred at room temperature for 20 hours. The reaction solution was filtered through celite, and then the solvent was evaporated under reduced pressure. Saturated aqueous sodium bicarbonate was added to the residue, followed by extraction with chloroform. The solvent was evaporated from the organic layer under reduced pressure to give a crude product of (5R)-5-{2-(4-chlorophenyl)-2-[6-methoxy-5-(1H-pyrazol-4-yl)pyridin-2-yl]ethyl}pyrrolidin-2-one as a yellow oil (77 mg).

Aufarbeitung

  1. filtrationThe reaction solution was filtered through celite
  2. customthe solvent was evaporated under reduced pressure
  3. additionSaturated aqueous sodium bicarbonate was added to the residue
  4. extractionfollowed by extraction with chloroform
  5. customThe solvent was evaporated from the organic layer under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cfdfa32d4e394908bc221ba32f40defc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822503B2

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