Research on two-ring 1-aza compounds

5-Hydroxymethyl-1,2-dihydropyrrolizines were catalytically hydrogenated to 3(5)-hydroxymethylpyrrolizidines, and the ratios of the isomers in the products of the reaction, which proceeds stereoselectively, were determined. The configuration of the diastereomers was established on the basis of the results of catalytic isomerization, a study of the chromatographic behavior of the isomers on a polar stationary phase, and a discussion of the isomeric composition of the hydrogenation products in the light of the general principles of the stereochemistry of catalytic hydrogenation. trans- and cis-3,8-H-3-Hydroxymethylpyrrolizidine and trans-3,8-H-3-methyl-trans-5,8-H-5-hydroxymethylpyrrolizidine were isolated from the mixtures of isomers. The existence of an intramolecular hydrogen bond in trans-3,8-H-3-hydroxymethyl- and trans-3,8-H-3-methyl-trans-5,8-H-5-hydroxymethylpyrrolizidine was shown by IR spectroscopy.See 1] for communication XIITranslated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 484–489, April, 1976.