Azabicycloalkanes as Analgetics. II. An Improved Synthesis of 1-Phenyl-6-azabicyclo [3,2,1] octane Derivatives
スポンサーリンク
概要
- 論文の詳細を見る
An improved synthesis of 6,7endo-dimethyl-1-(3-hydroxyphenyl)-6-azabicyclo [3,2,1]-octane (10c), a new analgetic agent with a low addiction liability, is described. Grignard reaction of 3-ethoxy-2-cyclohexen-1-one (1) with m-methoxyphenylmagnesium bromide gave the α, β-unsaturated ketone (2b). Hydrocyanation of the latter followed by methanolysis yielded the keto ester (5b). The bicyclic lactam (8b), a key intermediate in the original synthesis was obtained by reductive amination of 5b with methylamine. As a result of this sequence of reactions, 10c could be obtained in 7 steps from 1 in 42% overall yield. By an application of this new method, a number of 1-phenyl-6-azabicyclo [3,2,1] octane derivatives with various substituents on benzene ring (10d-k), nitrogen (31), and C_8 (39-46) have been prepared for pharmacological evaluation.
- 公益社団法人日本薬学会の論文
- 1976-07-25
著者
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井上 博純
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd, .
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武田 幹男
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,
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川森 政敏
Organic Chemistry Research Laboratory
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斉藤 清一
田辺製薬研
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斎藤 清一
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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斉藤 清一
Organic Chemistry Research Laboratory Tanabe Seiyaku Co . Ltd.
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塚本 悟郎
New Drug Research Laboratories Kanebo Ltd.
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本間 靖
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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武田 幹男
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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井上 博純
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd .
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野口 勝通
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd. :(present Address)sapporo Branch Tanab
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