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

HRID 1744883Notes

Reaction equation

HRID 1744883 reaction equation
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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-63470e7824a1469d96c8dfe4554001de
Source dataset
uspto-grants-2006_03
Patent number
US07019022B2

Reaction notes

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