Heteroalicyclic Aminoalkanol. II. Reactions of DL-2-Piperidinemethanol involving the Formation of DL-1-Azabicyclo[4,1,0]heptane

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概要

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• DL-2-Piperidinemethanol (I) was converted to O-acyl, 2-isothioureido and oxazolidine derivatives to be subjected to reactions such as acyl migration, transguanylation and oxidation with bromine respectively. The xanthate (XIII) derived from the N-methyl derivative of I (XII) was thermally rearranged to the corresponding dithiolcarbonate (XIV). In particular, I was converted to DL-1-azabicyclo[4,1,0]heptane (XXIV) via DL-2-piperidinemethanol hydrogen sulfate (XXIII). XXIV was easily polymerizable and therefore, stabilized in the form of picrate for identification. Structural proof for XXIV was provided from results of reactions to which it was subjected. In conclusion, the reaction sequences of I and XII were similar to those of acyclic analogues as be theoretically expected.

• 公益社団法人日本薬学会の論文
• 1965-03-25

著者

• 春日 成暉

  Faculty Of Pharmaceutical Sciences Kyushu University:(present Address) Sankyo Research Laboratories

• 田口 胤三

  Faculty of Pharmaceutical Sciences, Kyushu University

• 田口 胤三

  Faculty Of Pharmaceutical Sciences Kyushu University

関連論文

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• Catalytic Rearrangement of Xanthates to Dithiolcarbonates
• Rearrangement and trans-Elimination contrary to the Chugaev Reaction Rule. IX. Thermal Rearrangement of 2-Cycloalkenyl S-Alkyl Xanthate
• Rearrangement and trans-Elimination contrary to the Chugaev Reaction Rule. VIII. Thermal Rearrangement of 2-Alkenyl S-Alkyl Xanthate
• Heteroalicyclic Aminoalkanol. II. Reactions of DL-2-Piperidinemethanol involving the Formation of DL-1-Azabicyclo[4,1,0]heptane
• Heteroalicyclic Aminoalkanol. I. Syntheses of DL-2-Piperidinemethanol and meso-cis-2,6-Piperidinedimethanol and Reactions of Intermediates
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• Sulfinylamine Chemistry. I. A New Degradation Reaction of α-Amino Acid with N-Sulfinylaniline
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