Water → Tolterodine

HRID 29228

反応式

HRID 29228 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 443879Tolterodine収率 20.9%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-dcfc5940852349d2a6c25acb5c3b04d2
出典データセット
uspto-grants-2008_09
特許番号
US07420091B2

関連ノート

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