Syntheses of 1,2-N-Alkylimino-1,2,3,4-tetrahydronaphthalene Derivatives and Preparation of Ring Closed Analog of Salbutamol as a New β-Adrenoceptor Agent

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概要

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• A method for preparing 5-substituted 2-tertiary-alkylamino-6-hydroxy-1,2,3,4-tetrahydro-1-naphthalenols was described. The method involves the preparation of 1-alkylamino-2-hydroxy-1,2,3,4-tetrahydronaphthalenes from 2-bromo-1-hydroxy derivatives via 1,2-epoxides followed by the transposition of 1-alkylamino and 2-hydroxy groups via the ring closure to 1,2-aziridines. Formation of the epoxides and aziridines and the reaction of epoxides with amines were examined in detail. The ring-opening reaction of epoxides was regioselective and the attacking position of a nucleophile was not affected by the electronic effects of substituents on the benzene ring. Cyclization into aziridine rings was best accomplished by the Wenker method using a sulfur trioxide-triethylamine adduct as the sulfating agent. Using our process, trans-2-tert-butylamino-6-hydroxy-5-hydroxymethyl-1,2,3,4-tetrahydro-1-naphthalenol (70) was synthesized as conformationally fixed analog of salbutamol.

• 公益社団法人日本薬学会の論文
• 1978-02-25

著者

• 杉原 弘貞

  Central Research Division, Takeda Chemical Industries, Ltd.,

• 伊藤 克巳

  Central Research Division, Takeda Chemical Industries, Ltd.,

• 鵜川 清

  Central Research Division, Takeda Chemical Ind., Ltd.,

• 伊藤 克巳

  武田薬品工業

• 伊藤 克已

  Central Research Division Takeda Chemical Industries Ltd.

• 三宅 昭夫

  Central Research Division, Takeda Chemical Industries, Ltd.

• 三野 安

  Central Research Division, Takeda Chemical Industries, Ltd.

• 三宅 昭夫

  Central Research Division Takeda Chemical Industries Ltd.

• 杉原 弘貞

  Pharamaceutical Research Laboratories I Pharmaceutical Research Division Takeda Chemical Industries

• 杉原 弘貞

  Central Research Division Takeda Chemical Industries. Ltd.

• 鵜川 清

  Resarch & Development Division Takeda Chemical Industries Ltd.

• 三野 安

  Central Research Division Takeda Chemical Industries Ltd.

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