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2-Methylindole → 2-(1H-indol-2-ylmethyl)-1,1,1-trifluoro-4-(4-fluorophenyl)-4-methylpentan-2-ol

HRID 1510879
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Reaktionsgleichung

Reaktionsgleichung von HRID 1510879
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.C([Li])CCC.CC(C)([O-])C.[K+].[F:22][C:23]([F:38])([F:37])[C:24](=[O:36])[CH2:25][C:26]([C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)([CH3:28])[CH3:27]>C(OCC)C>[NH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[C:2]1[CH2:1][C:24]([OH:36])([CH2:25][C:26]([C:29]1[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=1)([CH3:28])[CH3:27])[C:23]([F:22])([F:38])[F:37]
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Komponenten

6

Edukt 4

HCID 72242-MethylindoleHCID 220326931,1,1-Trifluoro-4-(4-fluorophenyl)-4-methylpentan-2-oneHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium

Produkt 1

HCID 101264152-(1H-indol-2-ylmethyl)-1,1,1-trifluoro-4-(4-fluorophenyl)-4-methylpentan-2-olAusbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a diethyl ether solution of 53 mg of 2-methylindole was added 3 equivalents of n-butyl lithium followed by 90 mg of potassium tert-butoxide (t-BuOK) (solid) at room temperature. The mixture was allowed to stir for 30 minutes. 1,1,1-Trifluoro-4-(4-fluorophenyl)-4-methylpentan-2-one (100 mg) in diethyl ether was then added to the above mixture. The reaction was stirred at room for 1 hour. The reaction was quenched with saturated aqueous ammonium chloride, and extracted three times with EtOAc. The combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography to yield 40 mg of the title compound as a foam. Resolution to the (+)- and (−) enantiomers was accomplished by chiral HPLC on a CHIRALCEL® OD™ column, eluting with 10% isopropanol-hexanes.

Aufarbeitung

  1. stirringThe reaction was stirred at room for 1 hour
  2. customThe reaction was quenched with saturated aqueous ammonium chloride
  3. extractionextracted three times with EtOAc
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c6a3ac5ebb86443591e2071343e048a6
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08212040B2

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