複素環式化合物の合成研究 (第103報)
Coclaurine関連化合物の合成I dl-Coclaurineおよびdl-O-Benzyl-N-methylcoclaurineの合成
1965 年 85 巻 2 号 p. 166-168
詳細
1965 年 85 巻 2 号 p. 166-168
The Arndt-Eistert reaction between 2-diazo-4′-(methylsulfonyloxy) acetophenone (VI), easily obtained from p-cresol, and methoxy-4-benzyloxyphenethylamine afforded N-(3-methoxy-4-benzyloxyphenethyl)-2-p-(methylsulfonyloxyphenyl) acetamide (VII), which was converted to 1-p-(methylsulfonyloxybenzyl)-6-methoxy-7-benzyloxy-3, 4-dihydroisoquinoline (VIII) according to the Bischler-Napieralski reaction. After the reduction of methiodide (IX) of VIII to tetrahydroisoquinoline compound (X), dl-O-benzyl-N-methylcoclaurine (XI) was derived by treating X with alkali in a good yield, considered from the starting material (VI). Further debenzylation of XI by 20% hydrochloric acid gave dl-N-methylcoclaurine (II), which was confirmed. After the reduction of VIII by zinc dust in acetic acid, a treatment with alkali and then hydrochloric acid afforded dl-coclaurine (I), which is identical with the standard sample.
