Method for synthesis of (2S,3aS,7aS)-perhydroindole-2-carboxylic acid and esters thereof; and use in the synthesis of perindopril

Process for the preparation of (2S, 3aS, 7aS)-perhydroindole-2-carboxylic acid and its esters (I). Process for the preparation of (2S, 3aS, 7aS)-perhydroindole-2-carboxylic acid and its esters (I) by condensation of (2-hydroxymethyl) cyclohexanone (III) with a glycine ester (IV) in the presence of a...

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Bibliographic Details
Main Authors LANGLOIS, PASCAL, DUBUFFET, THIERRY
Format Patent
LanguageEnglish
French
German
Published 27.04.2005
Edition7
Subjects
CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
PEPTIDES
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Summary:Process for the preparation of (2S, 3aS, 7aS)-perhydroindole-2-carboxylic acid and its esters (I). Process for the preparation of (2S, 3aS, 7aS)-perhydroindole-2-carboxylic acid and its esters (I) by condensation of (2-hydroxymethyl) cyclohexanone (III) with a glycine ester (IV) in the presence of an organic base, to form a hexahydroindole carboxylic acid (V) which then undergoes catalytic hydrogenation to form a racemic mixture of perhydroindole carboxylic acids (VI). R = H, benzyl, or 1-6C alkyl. R1 = benzyl or 1-6C alkyl. The desired (2S, 3aS, 7aS) isomer is separated by resolution using a chiral amine to form (I). An Independent claim is included for the preparation of perindopril using (I) prepared by the new process.
Bibliography:Application Number: EP20030291420