Aluminium lithium hydride → dibenzyl-[2-(5,7-difluoro-1H-indol-3-yl)-1(S)-methyl-ethyl]-amine

HRID 1272237

Reaktionsgleichung

Reaktionsgleichung von HRID 1272237
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]([CH:22]([CH3:45])[CH:23]([C:25]1[C:33]2[C:28](=[C:29]([F:35])[CH:30]=[C:31]([F:34])[CH:32]=2)[N:27](S(C2C=CC=CC=2)(=O)=O)[CH:26]=1)O)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCOCC1.O1CCCC1>[CH2:15]([N:14]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C@@H:22]([CH3:45])[CH2:23][C:25]1[C:33]2[C:28](=[C:29]([F:35])[CH:30]=[C:31]([F:34])[CH:32]=2)[NH:27][CH:26]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 220148162-(N,N-dibenzylamino)-1-(1-benzenesulfonyl-5,7-difluoro-1H-indol-3-yl)-propan-1-ol

Produkt 1

HCID 20806555dibenzyl-[2-(5,7-difluoro-1H-indol-3-yl)-1(S)-methyl-ethyl]-amineAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22018518Dioxane tetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium aluminum hydride (LAH) (0.7 g, 18 mmol) is added portionwise to a dioxane/tetrahydrofuran (90 ml/10 ml) solution of 2-(N,N-dibenzylamino)-1-(1-benzenesulfonyl-5,7-difluoro-1H-indol-3-yl)-propan-1-ol (1.9 g, 3.3 mmol) under N2 at 0° C. After the addition is complete, the reaction is allowed to warm to room temperature, then is refluxed for 1 hour. The reaction is quenched with H2O and 15% aqueous NaOH, filtered, and the filtrate is diluted with ethyl acetate, washed with brine, dried (Na2SO4), filtered, concentrated, and the residue is purified by flash chromatography (SiO2, ethyl acetate/hexane gradient) to yield 1.2 g of dibenzyl-[2-(5,7-difluoro-1H-indol-3-yl)-1(S)-methyl-ethyl]-amine (86%).

Aufarbeitung

  1. additionAfter the addition
  2. temperatureis refluxed for 1 hour
  3. customThe reaction is quenched with H2O and 15% aqueous NaOH
  4. filtrationfiltered
  5. additionthe filtrate is diluted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe residue is purified by flash chromatography (SiO2, ethyl acetate/hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-0f83313de7e94dc48bcfb74a9f08d9e7
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208505B2

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