著者

坂井 進一郎 山中 悦二 横溝 理 松本 緑

出版者

公益社団法人 日本薬学会

雑誌

YAKUGAKU ZASSHI (ISSN:00316903)

巻号頁・発行日

vol.95, no.12, pp.1511-1516, 1975-12-25 (Released:2008-05-30)

参考文献数

10

被引用文献数

1 2

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It has been found that a reaction of the cyclic imino ether in gardneramine (I) with MeI afforded N-methylated oxindole (III). Synthesis of a compound (XIV)) having a cyclic imino ether system and its reaction with MeI are described. An alcohol (X) was prepared by the Michael reaction of N-acetyl-3-ethyloxindole (VII) with ethyl acrylate, followed by LiA1H4 reduction. On treatment with p-toluenesulfonyl chloride in pyridine, X afforded a tosylate (XI) and a chloride (XII). The imino ether (XIV), synthesised by the reaction of XII with potassium t-butoxide in dimethyl sulfoxide-benzene (1 : 1), reacted with MeI to afford N-methyl-3-(3-iodopropyl)oxindole (XX). The reductive dehalogenation of XX with NaBH4/Me2SO gave N-methyl-3-ethyl-3-propyloxindole (XXI), which was identical with the authentic sample prepared from XII by a different route.