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Details for Patent: 4,727,160

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Details for Patent: 4,727,160

Title: Method for making 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, DE), Becker; Reinhard (Wiesbaden, DE), Scholkens; Bernward (Kelkheim, DE)
Assignee: Hoechst Aktiengesellschaft (Frankfurt am Main, DE)
Filing Date:Oct 09, 1984
Application Number:06/658,902
Claims:1. A method for making a compound of the formula ##STR11## or a salt thereof with an acid or a base, wherein the hydrogen atoms on the bridge-head carbon atoms in the 1- and 5-positions are in the cis-configuration relative to one another and the carboxyl group on the carbon atom in the 3-position is orientated in the endo-position relative to the bicyclic ring system, and wherein W is hydrogen, alkyl having 1-6 carbon atoms, or aralkyl having 7 or 8 carbon atoms, which method comprises cyclizing a compound of the formula ##STR12## wherein Y.sup.1 is alkanoyl having 1 to 5 carbon atoms or aroyl having 7 to 9 carbon atoms and

R.sup.2 is alkyl having 1 to 5 carbon atoms or aralkyl having 7 to 9 carbon atoms,

with a strong acid, with acylamide and ester cleavage, to give an intermediate compound of the formula ##STR13## catalytically hydrogenating this intermediate compound to form the desired compound wherein W is hydrogen in the presence of a transition metal catalyst or by reducing said intermediate with a borane-amine complex or a complex borohydride in a lower alcohol, and then optionally esterifying the acid product to give a compound wherein W is alkyl having 1 to 6 carbon atoms or aralkyl having 7 or 8 carbon atoms.

2. A method as in claim 1 wherein said compound of the formula ##STR14## is obtained by reacting an enamine of the formula ##STR15## wherein X.sup.1 is dialkylamino having 2 to 10 carbon atoms or is ##STR16## wherein m and o are each integers from 1 to 3 and (m+o)=3 and A is --CH.sub.2 --, --NH--, --O--, or --S--, with an N-acylated .beta.-halogeno-.alpha.-amino-carboxylic acid ester of the formula ##STR17## wherein X.sup.2 is chlorine or bromine, or with an acrylic acid of the formula ##STR18##
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