Synthesis of N-Methyl-2-[8-(3,4-dimethoxyphenyl)-1,4-dioxaspiro-[4,5] decan-8-yl] ethylamine

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概要

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• For the studies on modification of mesembrine (II), N-methyl-2-[8-(3,4-dimethoxyphenyl)-1,4-dioxaspiro [4,5] decan-8-yl] ethylamine (I) was synthesized from 1,4-dioxaspiro [4,5] decan-8-one (III) : the Cope reaction of III with ethyl cyanoacetate gave 1,4-dioxaspiro [4,5] decan-8-ylidene cyanoacetate (IV), whose Grignard reaction with 4-halogeno-1,2-dimethoxybenzene afforded ethyl 8-(3,4-dimethoxyphenyl)-1,4-dioxaspiro-[4,5] decane-8-cyanoacetate (V). Hydrolysis of V followed by decarboxylation gave 8-(3,4-dimethoxyphenyl)-1,4-dioxaspiro [4,5] decane-8-acetonitrile (VIII), which was reduced with LiAlH_4 to obtain 2-[8-(3,4-dimethoxyphenyl)-1,4-dioxaspiro [4,5] decan-8-yl]-ethylamine (IX). Treatment of IX with ethyl chloroformate followed by reduction with LiAlH_4 furnished I.

• 公益社団法人日本薬学会の論文
• 1976-05-25

著者

• 伊藤 磯雄

  名古屋市立大学薬学部

• 織田 範一

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 伊藤 磯雄

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 永井 愼一

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 植田 泰誠

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 久米 茂行

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 久米 茂行

  Faculty Of Pharmaceutical Sciences Nagoya City University

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