A method was developed for the synthesis of derivatives of 3-substituted pyrrolidines from activated alkenes by 1,3-dipolar cycloaddition of unstable 2-benzylazomethylide, generated in situ from N-benzyl-N-(methoxymethyl)-N-(trimethylsilyl)amine. A method was developed for the reduction of 4-(3-pyrrolidyl)pyridine, prepared by the above-mentioned method, to the corresponding derivatives of (3-pyrrolidyl)piperidine with high yields under mild conditions.The enormous interest in the various derivatives of pyrrolidine is due to the wide range of biological activity exhibited by these heterocyclic compounds. The development of a universal method for the synthesis of the pyrrolidine ring under mild conditions is the most important problem in the synthesis of alkaloids and their derivatives. In spite of the fact that a large number of the most varied compounds containing a pyrrolidine ring have been synthesized, no methods have been published for the synthesis of 4-pyrrolidylpiperidine derivatives that would provide interesting models for various synthetic transformations both at the nitrogen atom of the piperidine ring and at the nitrogen atom of the pyrrolidine ring. Our investigation concerned the synthesis of compounds that are interesting from the standpoint both of combinatorial chemistry and of possible use in laboratory synthesis.We produced the 3-substituted pyrrolidines by 1,3-dipolar cycloaddition of the little-known unstable azomethine ylide to various olefins containing electron-withdrawing groups as substituents at the double bond [1, 2]. The reagent was generated in situ from N-benzyl-N-(methoxymethyl)-N-(trimethylsilylmethyl)amine (1) in polar solvents in the presence of a catalyst. Apart from the main olefin (4-vinylpyridine) that we needed for the production of the required pyrrolidylpyridine, we used styrene and benzyl acrylate as model compounds. The use of such olefins in the this reaction with various types of catalyst (F -, protic acids, Lewis acids) has been described. However, no systematic investigations into the effect of the nature of the catalyst and the reaction conditions on the course of the process have been described in the literature [2,3].In addition, the use of the costly and unstable N-benzyl-N-(methoxymethyl)-N-(trimethylsilylmethyl)amine (1) as starting compound prevented the widespread application of such a method for the construction of the pyrrolidine ring. For this reason we decided, first of all, to optimize the method for the preparation of the amine 1. A method for the synthesis of the amine 1 by the successive alkylation of benzylamine with chloromethyltrimethylsilylmethane followed by transformation into the corresponding tertiary amine by the action of a 37% aqueous solution of formaldehyde in methanol at low temperature was described _______ * Dedicated to E. J. Lukevics on his 70th birthday __________________________________________________________________________________________

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