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Details for Patent: 4,879,403

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Details for Patent: 4,879,403

Title: Process for the preparation of cis, endo-2-azabicyclo-[3.3.0]-octane-3-carboxylic acids
Abstract:Compounds of the formula I ##STR1## in which the carboxyl group on carbon atom 3 is orientated in the endo-position relative to the bicyclic ring system of cis-configuration, and in which R.sup.1 denotes hydrogen, allyl, vinyl or a side-chain of a naturally occurring .alpha.-aminoacid, which may be protected, R.sup.2 denotes hydrogen, alkyl, alkenyl or aralkyl, Y denotes hydrogen or hydroxyl and Z denotes hydrogen, or Y and Z together denote oxygen, and X denotes alkyl, alkenyl or cycloalkyl, or aryl which is optionally mono-, di- or tri-substituted by alkyl, alkoxy, hydroxyl, halogen, nitro, amino, alkylamino, dialkylamino or methylenedioxy, or denotes indol-3-yl, a process for their preparation, agents containing these compounds and their use.
Inventor(s): Teetz; Volker (Hofheim am Taunus, DE), Geiger; Rolf (Frankfurt am Main, DE), Urbach; Hansjorg (Kronberg/Taunus, DE), Becker; Reinhard (Wiesbaden, DE), Scholkens; Bernward (Kelkheim, DE)
Assignee: Hoechst Aktiengesellschaft (Frankfurt am Main, DE)
Filing Date:Nov 02, 1988
Application Number:07/267,753
Claims:1. A method for making a compound of the formula ##STR11## wherein the chirality centers labelled with an asterisk both have the S-configuration and wherein

R.sup.1 is methyl or 4-aminobutyl, which may be acylated;

R.sup.2 is (C.sub.1 -C.sub.6)-alkyl;

X is (C.sub.1 -C.sub.6)-alkyl, (C.sub.2 -C.sub.6)-alkenyl, (C.sub.5 -C.sub.9)-cycloalkyl or (C.sub.6 -C.sub.12)-aryl, which can be mono-, di- or trisubstituted by (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, hydroxyl, halogen, nitro, amino, (C.sub.1 -C.sub.4)-alkylamino, di-(C.sub.1 -C.sub.4)-alkylamino, and/or by methylenedioxy, or

X is indol-3-yl; and

W' is an esterifying group removable by hydrogenolysis, which method comprises reacting an S-alpha-aminoacid ester of the formula

with a keto-acrylic acid ester of the formula

to give a reaction product predominantly containing the desired compound and then isolating the desired compound from said reaction product by crystallization.

2. A method as in claim 1 wherein R.sup.1 is methyl or 4-aminobutyl, which may be acylated; R.sup.2 is methyl or ethyl; and X is phenyl or phenyl which is mono- or di-substituted by fluorine and/or chlorine.

3. A method as in claim 1 wherein R.sup.1 is methyl, R.sup.2 is ethyl, and X is phenyl.

4. A method for making a compound of the formula ##STR12## wherein the chirality centers labelled with an asterisk both have the S-configuration and wherein

R.sup.1 is methyl or 4-aminobutyl, which may be acylated;

R.sup.2 is (C.sub.1 -C.sub.6)-alkyl;

X is (C.sub.1 -C.sub.6)-alkyl, (C.sub.2 -C.sub.6)-alkenyl, (C.sub.5 -C.sub.9)-cycloalkyl or (C.sub.6 -C.sub.12)-aryl, which can be mono-, di- or tri- substituted by (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, hydroxyl, halogen, nitro, amino, (C.sub.1 -C.sub.4)-alkylamino, di-(C.sub.1 -C.sub.4)-alkylamino, and/or by methylenedioxy, or

X is indol-3-yl;

which method comprises reacting an S-alpha-aminoacid ester of the formula

wherein

W' is an esterifying group removable by hydrogenolysis,

with a keto-acrylic acid ester of the formula

to give a reaction product of the formula ##STR13## predominantly comprising a desired stereoisomer wherein the chirality centers labelled with an asterisk both have the S-configuration, isolating the desired stereoisomer from said reaction product by crystallization, and then reducing the desired compound by hydrogenation, whereby W' is removed by hydrogenolysis.

5. A method as in claim 4 wherein R.sup.1 is methyl or 4-aminobutyl, which may be acylated; R.sup.2 is methyl or ethyl; and X is phenyl or phenyl which is mono- or di-substituted by fluorine and/or chlorine.
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