Tributylphosphine → Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(2-(methylthio)ethoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 237448Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237448
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:26]2[C:31]([CH3:32])=[CH:30][C:29]([OH:33])=[CH:28][C:27]=2[CH3:34])=[C:6]2[C:10]=1[C@H:9]([O:11][C:12]1[CH:25]=[CH:24][C:15]3[C@H:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:17][O:18][C:14]=3[CH:13]=1)[CH2:8][CH2:7]2.[CH3:35][S:36][CH2:37][CH2:38]O.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:34][C:27]1[CH:28]=[C:29]([O:33][CH2:38][CH2:37][S:36][CH3:35])[CH:30]=[C:31]([CH3:32])[C:26]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[C:10]2[C:6]=1[CH2:7][CH2:8][C@H:9]2[O:11][C:12]1[CH:25]=[CH:24][C:15]2[C@H:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:17][O:18][C:14]=2[CH:13]=1

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 789252-(Methylthio)ethanolHCID 86697113Methyl 2-((S)-6-((R)-7-fluoro-4-(4-hydroxy-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Produkt 1

HCID 86697114Methyl 2-((S)-6-((R)-4-(2,6-dimethyl-4-(2-(methylthio)ethoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-((S)-6-((R)-7-fluoro-4-(4-hydroxy-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (280 mg) and 2-(methylthio)-ethanol (54 μL) in toluene (8 mL) are successively added 1,1′-(azodicarbonyl)-dipiperidine (240 mg) and tributylphosphine (240 mL). The mixture is stirred for 12 hours at room temperature, partitioned between saturated aqueous NaHCO3 solution and dichloromethane and stirred for 30 minutes. The phases are separated and the organic phase is dried (MgSO4). The solvents are evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→70:30) to give the title compound. Yield: 235 mg; LC (method 4): tR=1.97 min; Mass spectrum (ESI+): m/z=537 [M+H]+.

Aufarbeitung

  1. custompartitioned between saturated aqueous NaHCO3 solution and dichloromethane
  2. stirringstirred for 30 minutes
  3. customThe phases are separated
  4. dry with materialthe organic phase is dried (MgSO4)
  5. customThe solvents are evaporated
  6. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→70:30)

Quellen und Nachweise

ORD-Eintrag
ord-2fdc42aaa62e49c4826c7d38d06c9a01
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642585B2

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