Water → Tolterodine

HRID 29228

반응식

HRID 29228 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 443879Tolterodine수율 20.9%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-dcfc5940852349d2a6c25acb5c3b04d2
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420091B2

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