ChemInform Abstract: Application of 1,2,3,5,6,7‐Hexahydropyrrolizinium Perchlorate in the Synthesis of 7a‐Substituted Hexahydro‐1H‐pyrrolizines.

Abstract

158ChemInform Abstract The hexahydro-1H-pyrrolizines (III) are prepared from the perchlorate (I) and the Grignard compounds (II). (IIIc) is converted to the salt (IV) which is cleaved and hydrogenated to form the perhydroazocine (V). (I) reacts with the malonate (VI) to give the adduct (VII). The enamine (VIII) and its dimer (IX) are obtained by treatment of (I) with bases. Reaction of (VIII) and (IX) with the malonic acid derivatives (X) produces the adducts (XI). The ester (XII) derived from (XIb) and (XIb) itself is reduced to give the alcohol (XIII) or the amine (XIV).