Synthesis of Homoesermethole.

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概要

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• α-Bromo-α-methyl-δ-phthalimidovaler-p-anisidide (VIII) was fused with aluminum chloride according to Stolle to give 5-methoxy-1,3-dimethyl-3-(γ-phthalimidopropyl) oxindole (IX) after methylation. Phthalimido group could be readily removed from this compound by the standard method, furnishing 3-(γ-aminopropyl) oxindole derivative (X), which was then monomethylated to (XI). This compound could also be prepared advantageously by reducing 5-methoxy-1,3-dimethyl-3-(β-cyanoethyl) oxindole (XII) catalytically in the presence of methylamine. On being reduced with sodium in boiling ethanol the latter gave rise to a single dl-homoesermethole (III) in a fair yield, no isomeric base being detected in the reduction product.

• 公益社団法人日本薬学会の論文
• 1958-04-20

著者

• 菅沢 重彦

  Pharmaceutical Institute Medical Faculty University of Tokyo

• 村山 正雄

  Research And Development Laboratory Nippon Shinyaku Co. Ltd.

• 村山 正雄

  Pharmaceutical Institute, Medical Faculty, University of Tokyo

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