Water → Tolterodine

HRID 29228

Reaction equation

HRID 29228 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 443879TolterodineYield 20.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-dcfc5940852349d2a6c25acb5c3b04d2
Source dataset
uspto-grants-2008_09
Patent number
US07420091B2

Linked notes

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