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

抄録

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.