Water → Tolterodine

HRID 29228

Reaktionsgleichung

Reaktionsgleichung von HRID 29228
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[CH:15]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:16][C:17]([N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=O.O>CCOCC>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([OH:7])=[C:9]([C@@H:15]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:16][CH2:17][N:19]([CH:20]([CH3:22])[CH3:21])[CH:23]([CH3:24])[CH3:25])[CH:10]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 11551832N,N-diisopropyl-3-phenyl-3-(2-hydroxy-5-methylphenyl)propionamideHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 443879TolterodineAusbeute 20,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A suspension of lithium aluminium hydride (3 g, 0.08 mols) in 350 ml of anhydrous ether is added with 0.5 g of 3-(2-hydroxy-5-methyl-phenyl)-N,N-diisopropyl-3-phenyl-propionamide in portions. The mixture is refluxed while stirring for 4 days. Afterwards, water is carefully added to destroy the lithium aluminium hydride excess, the mixture is acidified to pH 5 with acetic acid, the ether phase is separated and dried over sodium sulfate. The solvent is evaporated to obtain an oil which is purified by flash chromatography (eluent hexane-ethyl acetate 7:3). 0.1 g of tolterodine free base are obtained.

Aufarbeitung

  1. temperatureThe mixture is refluxed
  2. customto destroy the lithium aluminium hydride excess
  3. customthe ether phase is separated
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is evaporated
  6. customto obtain an oil which
  7. customis purified by flash chromatography (eluent hexane-ethyl acetate 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-dcfc5940852349d2a6c25acb5c3b04d2
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420091B2

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