A synthesis of 1-azabicyclo[2.2.1]heptane-3-carboxylic acid esters in enantiomerically pure form
1991; Issue: 5 Linguagem: Inglês
10.1039/p19910001091
ISSN2050-8255
AutoresIan F. Cottrell, David Hands, Derek J. Kennedy, Kerensa J. Paul, Stanley H. B. Wright, Karst Hoogsteen,
Tópico(s)Analytical Chemistry and Chromatography
ResumoA novel synthesis of ethyl 1-azabicyclo[2.2.1]heptane-3-carboxylate via 1-benzylperhydropyrano[3,4-c]pyrrol-4-one and 1-benzyl-3-(2-bromoethyl)-4-ethoxycarbonylpyrrolidinium bromide is described. Modification of the method, by incorporation of a chiral substituted benzyl group on the nitrogen atom, has led to the first reported process for the preparation of these esters in enantiomerically pure form. The absolute configuration of the bicyclic esters was deduced by X-ray crystallography of an intermediate, 2-[(S)-1-phenylethyl]perhydropyrano[3,4-c]pyrrole-4-one.
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