Studies on the Syntheses of Heterocyclic Compounds. LXII. Synthesis of rac-Tetrahydrorotundine.
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概要
- 論文の詳細を見る
2-Methyl-3-ethoxycarbonyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzo [a] quinolizinium salt was prepared by cyclization of the piperidone compound synthesized by the condensation of 3,4-dimethoxyphenethyl bromide and 4-methyl-5-ethoxycarbonyl-2-piperidone in the presence of sodium hydride. Its amino derivative was prepared by the Curtius degradation, via the hydrazide, azide, and benzylurethan. The amino compound was diazotized with sodium nitrite in acetic acid and converted to the hydroxyl derivative, which was purified as its methiodide. In order to prove the presence of this hydroxyl group, the compound was led to its methanesulfonate. The hydroxy base was methylated with diazomethane, in the presence of fluoroboric acid in chloroform, and the objective methyl ether, i.e. rac-tetrahydrorotundine, was obtained as its methiodide. Some discussions were made on the reaction of aliphatic primary amines with nitrous acid.
- 社団法人日本薬学会の論文
- 1961-02-25
著者
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亀谷 哲治
Pharmaceutical Institute, Tohoku University School of Medicine
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野村 幸雄
Pharmaceutical Institute School Of Medicine Tohoku University
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亀谷 哲治
Institute Of Medicinal Chemistry Hoshi University
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亀谷 哲治
Pharmaceutical Institute Medical Faculty University Of Osaka
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亀谷 哲治
Toyama Technical College
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野村 幸雄
Pharmaceutical Faculty University Of Osaka
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