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摘 要:,C15H23NO3,265.3555,tert-Butyl N-[(3S)-3-hydroxy-3-phenylpropyl]-N-methylcarbamate
  • 【化學名】tert-Butyl N-[(3S)-3-hydroxy-3-phenylpropyl]-N-methylcarbamate
  • 【CAS登記號】
  • 【結構式】,C15H23NO3,265.3555,tert-Butyl N-[(3S)-3-hydroxy-3-phenylpro--藥物合成數據庫
  • 【分子式】C15H23NO3
  • 【分子量】265.3555
  • 【來源】
  • 【合成情況】 
  • 〖目標產物〗Atomoxetine hydrochloride, Tomoxetine hydrochloride, LY-139602 [(+)-isomer], LY-135252(racemate), LY-139603, Strattera
  • 〖合成路線〗
  • 〖合成方法〗A new synthesis for tomoxetine hydrochloride has been reported: The reduction of benzoylacetic acid ethyl ester (I) with Baker's yeast and glucose in water, or the enzymatic hydrolysis of 3-acetoxy-3-phenylpropionic acid ethyl ester (II), gives (-)-3-hydroxy-3-phenylpropionic acid ethyl ester (III), which by reaction with methylamine yields the corresponding amide (IV). The reduction of (IV) with LiAlH4 in ether affords (-)-3-hydroxy-N-methyl-3-phenylpropylamine (V), which is protected with di-tert-butyldicarbonate to the amide (VI). The condensation of (VI) with o-cresol (VII) by means of triphenylphosphine and diethylazodicarboxylate (DEAD) in ether yields the protected final product (VIII), which is finally deprotected with dry HCl in methanol.
  • 〖參考〗Dike, S.Y.; Kumar, A.; Ner, D.H.; A new chemoenzymatic enantioselective synthesis of R-(-)-tomoxetine, (R)-fluoxetine and (S)-fluoxetine. Tetrahedron Lett 1991, 32, 16, 1901
 
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