Studies on the Syntheses of Heterocyclic Compounds. DCXXVI. A Modified Synthesis of Pentazocine

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概要

• 論文の詳細を見る

• Pentazocine (1) was synthesized from L-tyrosine (2). N-Benzylation of methyl ester (3), obtained from L-tyrosine, followed by Schotten-Baumann reaction of the amine (4), gave the amide (5). Dieckmann reaction of 5 gave the racemic β-ketoester (6), whose methylation followed by decarboxylation afforded the ketoamide (8). Grignard reaction gave the carbinol (9), which was cyclized with hydrobromic acid to afford the amide (10) in good yield. Reduction of 10 with sodium bis-(2-methoxyethoxy) aluminum hydride or lithium aluminum hydride gave the amine (11), which had already been converted into pentazocine.

• 社団法人日本薬学会の論文
• 1975-09-25

著者

• 亀谷 哲治

  Pharmaceutical Institute, Tohoku University School of Medicine

• 福本 圭一郎

  東北大・薬

• 福本 圭一郎

  Pharmaceutical Institute, Tohoku University

• 井原 正隆

  Pharmaceutical Institute, Tohoku University

• 井原 正隆

  東北大薬

• 井原 正隆

  Graduate School Of Pharmaceutical Sciences Tohoku University

• 黄 世平

  東北大学薬学部

• 黄 世平

  Pharmaceutical Institute, Tohoku University

• 亀谷 哲治

  Pharmaceutical Institute Medical Faculty University Of Osaka

• 福本 圭一郎

  Pharmaceutical Institute Tohoku University School Of Medicine

• Ihara Masataka

  Department Of Organic Chemistry Graduate School Of Pharmaceutical Sciences Tohoku University

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