ニトロパラフィンに関する研究 (第9報) : 2-ニトロプロパンよりα-アミノイソ酪酸の生成

概要

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As one of the method of utilization of nitroparaffin, the nitro alcohol obtained by condensation with aldehyde was reduced to give corresponding amino alcohol and oxidation of this to amino acid has been attempted. 2-Amino-2-methyl-l-propanol, prepared from 2-nitropropane and formaldehyde, was used as a starting material. In the oxidation of hydroxyl group, the amino group was protected from oxidation by the benzoylation with benzoyl chloride, and the oxidation was carried out by using three kinds of oxidizing agents. It was found that potassium permanganate was the most superior oxidizing agent and the oxidation was effective to give above 90% yield of product. For debenzoylation reaction, it was treated with a dilute hydrochloric acid for deriving it into objective amino acid hydrochloride, it was dehydrochlorinated by use of amine to give α-aminoisobutyric acid. Using of aniline as the amine was suitable. Each of the above reaction was found to be proceeded smoothly. The structures of intermediate products were examined by infrared absorption spectra and the mechanisms of reactions were clarified.
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