Novel method for synthesising (2S, 3aS, 7aS)-perhydroindole-2-carboxylic acid and the esters thereof and the use thereof for perindopril synthesis

Production of (2S,3aS,7aS)-perhydroindole-2-carboxylic acid derivatives (I) comprises reacting 1-(1-cyclohexenyl)pyrrolidine (III) with a N-protected 3-iodoalanine derivative (IV), deprotecting the amino group, cyclizing and dehydrating the product, catalytically hydrogenating the product at 1-30 ba...

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Bibliographic Details
Main Authors THIERRY DUBUFFET, PASCAL LANGLOIS
Format Patent
LanguageEnglish
Published 16.09.2004
Edition7
Subjects
CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
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Summary:Production of (2S,3aS,7aS)-perhydroindole-2-carboxylic acid derivatives (I) comprises reacting 1-(1-cyclohexenyl)pyrrolidine (III) with a N-protected 3-iodoalanine derivative (IV), deprotecting the amino group, cyclizing and dehydrating the product, catalytically hydrogenating the product at 1-30 bar, and optionally deprotecting or reprotecting the acid group. Production of compounds of formula (I) comprises reacting 1-(1-cyclohexenyl)pyrrolidine (III) with a N-protected 3-iodoalanine compound of formula (IV) to give a product of formula (V), deprotecting the amino group and cyclizing and dehydrating the product to give a compound of formula (VI), and catalytically hydrogenating (VI) at 1-30 bar and optionally deprotecting or reprotecting the acid group. R = H or a protecting group, and R' = a protecting group. An Independent claim is also included for production (unspecified) of perindopril or its salts from (I) produced as above.
Bibliography:Application Number: AU20040218200