Methanol → methyl [(1R)-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetate

HRID 1744883

Reaktionsgleichung

Reaktionsgleichung von HRID 1744883
ClC1C=CC([C@@H]([N:10]2[C:22]3[C@@H:21]([CH2:23][C:24]([OH:26])=[O:25])[CH2:20][CH2:19][CH2:18][C:17]=3[C:16]3[C:11]2=[C:12]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:13]=[C:14]([F:27])[CH:15]=3)C)=CC=1.[CH3:32]O>[Pd]>[CH3:32][O:26][C:24](=[O:25])[CH2:23][C@@H:21]1[C:22]2[NH:10][C:11]3[C:16](=[CH:15][C:14]([F:27])=[CH:13][C:12]=3[S:28]([CH3:31])(=[O:29])=[O:30])[C:17]=2[CH2:18][CH2:19][CH2:20]1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 112597972-((R)-9-((S)-1-(4-chlorophenyl)ethyl)-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl)acetic acid

Produkt 1

HCID 58607117methyl [(1R)-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

To a solution of [(1R)-9-[(1S)-1-(4-chlorophenyl)ethyl]-6-fluoro-8-(methylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]acetic acid ([α]D=−226° in MeOH) in MeOH (0.1M) was added 10% palladium on carbon (10% wt/wt). A stream of N2 was bubbled through the mixture for 5 min. The reaction was stirred at rt under H2 atmosphere (balloon) for 24 hrs and filtered through a celite pad eluted with CH2Cl2. The solvents were removed by evaporation under reduced pressure and the residue was swished in MeOH to give the title compound.

Aufarbeitung

  1. customA stream of N2 was bubbled through the mixture for 5 min
  2. filtrationfiltered through a celite pad
  3. washeluted with CH2Cl2
  4. customThe solvents were removed by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-63470e7824a1469d96c8dfe4554001de
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07019022B2

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