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Synthesis 2009(19): 3327-3331
DOI: 10.1055/s-0029-1216963
DOI: 10.1055/s-0029-1216963
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of a Conformationally Rigid Analogue of 2-Aminoadipic Acid Containing an 8-Azabicyclo[3.2.1]octane Skeleton
Further Information
Publication History
Received
11 May 2009
Publication Date:
21 August 2009 (online)


Abstract
A new, conformationally rigid analogue of 2-aminoadipic acid, 8-[(benzyloxy)carbonyl]-3-methylene-8-azabicyclo[3.2.1]octane-1,5-dicarboxylic acid, is synthesized from dimethyl rac-2,5-dibromohexanedioate. The key steps involve alkylation-cyclization of 1-benzyl 2,5-dimethyl pyrrolidine-1,2,5-tricarboxylate with 3-chloro-2-(chloromethyl)prop-1-ene to yield the 8-azabicyclo[3.2.1]octane skeleton.
Key words
conformational restriction - bicyclic compounds - pyrrolidines - alkylations - cyclization