2-((S)-6-((R)-4-(4-(2,5-Dihydrofuran-3-yl)-2,6-dimethylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid → 2-((3S)-6-((1R)-4-(2,6-Dimethyl-4-(tetrahydrofuran-3-yl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 237722Notes

Reaction equation

HRID 237722 reaction equation
[O:1]1[CH2:5][CH:4]=[C:3]([C:6]2[CH:11]=[C:10]([CH3:12])[C:9]([C:13]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]4[C:14]=3[CH2:15][CH2:16][C@H:17]4[O:23][C:24]3[CH:36]=[CH:35][C:27]4[C@H:28]([CH2:31][C:32]([OH:34])=[O:33])[CH2:29][O:30][C:26]=4[CH:25]=3)=[C:8]([CH3:37])[CH:7]=2)[CH2:2]1>C(OCC)(=O)C.[Pd]>[CH3:12][C:10]1[CH:11]=[C:6]([CH:3]2[CH2:4][CH2:5][O:1][CH2:2]2)[CH:7]=[C:8]([CH3:37])[C:9]=1[C:13]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]2[C:14]=1[CH2:15][CH2:16][C@H:17]2[O:23][C:24]1[CH:36]=[CH:35][C:27]2[C@H:28]([CH2:31][C:32]([OH:34])=[O:33])[CH2:29][O:30][C:26]=2[CH:25]=1

Participants

4

Reactant 1

HCID 866972482-((S)-6-((R)-4-(4-(2,5-Dihydrofuran-3-yl)-2,6-dimethylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

Product 1

HCID 866973912-((3S)-6-((1R)-4-(2,6-Dimethyl-4-(tetrahydrofuran-3-yl)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The title compound is prepared from 2-((S)-6-((R)-4-(4-(2,5-dihydrofuran-3-yl)-2,6-dimethylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid by hydrogenation in the presence of palladium (10% on carbon) in ethyl acetate at room temperature. LC (method 9): tR=1.17 min; Mass spectrum (ESI+): m/z=503 [M+H]+.

Sources & evidence

ORD record
ord-9ddb155cac034aa2b87888830343af97
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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