Synthesis of N,N′-Unsymmetrical 9-Amino-5,7-dimethyl-bispidines

Abstract

A new approach to the preparation of N,N′-unsymmetrically substituted 9-aminobispidines through aminal bridge removal reaction has been developed, the principal feature of which is the ability to selectively functionalize all three nitrogen atoms. The intermediates of 1,3diazaadamantane's aminal bridge removal reaction are characterized, and the mechanism of this reaction is proposed based on the analysis of their structures. Representatives of the previously unknown saturated heterocyclic 1,5,9-triazatricyclo[5.3.1.0 3,8 ]undecane system were obtained and structurally characterized. Thus, it was possible for the first time to obtain 3,7,9trisubstituted bispidines containing acetyl, Boc, and benzyl groups at nitrogen atoms, which can be independently removed (orthogonal protective groups).