1955 年 75 巻 12 号 p. 1461-1466
Some time ago, Ueno and others obtained alkylpyrrolidine by the reduction of N-methyldihydrokaininediol or N-methyldihydrokainine dichloride, derived from kainic acid, and from the results of its Hofmann degradation and other reactions, assumed the structure of 1, 2-dimethyl-3-ethyl-4-isopropylpyrrolidine for the alkylpyrrolidine. This compound was prepared and its first-stage Hofmann degradation and reduction of the methine thereby obtained afforded a dihydromethine compound, possessing only one asymmetric carbon. The infrared absorption spectra of its methiodide, m.p. 186-187°, and that of dihydromethine methiodide, m.p. 207°, [α]D18: -11.5±0.5° (c=1, MeOH), derived from kainic acid, measured in chloroform, agreed in every respect. This has confirmed the alkylpyrrolidine structure and also offered one evidence for the appropriateness of the planar structure of kainic acid proposed earlier.