Ethanol → (R)-5-Methyl-3-[(pyrrolidin-2-yl)carbonyl]-1H-indole

HRID 610054

Reaktionsgleichung

Reaktionsgleichung von HRID 610054
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][CH2:12][OH:13]>CCOC(C)=O.[Pd]>[NH3:7].[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:12]([C@H:11]1[CH2:4][CH2:5][CH2:6][NH:7]1)=[O:13]

Komponenten

6

Edukt 2

HCID 702EthanolHCID 119785-Methylindole

Produkt 2

HCID 222AmmoniaHCID 54138762(R)-5-Methyl-3-[(pyrrolidin-2-yl)carbonyl]-1H-indoleAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl)]-5-methyl-1H-indole (Example 5b) in EtOAc (10 mL) was added EtOH (10 mL) and Pd/C (1.3 g). The reaction mixture was stirred at room temperature under a hydrogen atmosphere until the starting material was consumed. At this time, the reaction mixture was filtered through celite and the solvent was evaporated. The crude product was purified by column chromatography (4:1 CHCl3 : NH3 (2M in MeOH) to yield the title compound (121.5 mg, 15%) as a white solid (mp 194-196° C.).

Aufarbeitung

  1. customwas consumed
  2. filtrationAt this time, the reaction mixture was filtered through celite
  3. customthe solvent was evaporated
  4. customThe crude product was purified by column chromatography (4:1 CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-d62deb98251646318f3c6835cfcebfff
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998462

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