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Racemates of optically active bicyclic imino-alpha-carboxylic esters
| Details |
Inventors: Geiger, Rolf; Teetz, Volker; Langner, Dietrich;
Assignee: Hoechst Aktiengesellschaft (DE)
Primary Examiner: Hollrah; Glennon H.
Assistant Examiner: Springer; D. B.
Attorney, Agent or Firm: Finnegan, Henderson, Farabow, Garrett & Dunner
The invention relates to a process for resolving racemic mixtures of bicyclic imino-.alpha.-carboxylic esters into the components by crystallization of diastereomeric salts, which comprises preparing the salts of the racemic esters with optically active N-acylated R- or S-aminocarboxylic acid which contain a phenyl nucleus, recrystallizing them from an organic solvent, decomposing the precipitated, optically homogeneous diastereomeric salts in a manner known per se, and isolating the enantiomers and, where appropriate, converting the latter into the free acids by hydrolysis in a manner known per se. The invention also relates to optically pure compounds of the formula ##STR1## and to diastereomeric salts of these compounds, in which two of the radicals A, B.sup.1, B.sup.2 and C form a carbon chain and the others denote hydrogen, and R is an esterifying group. |
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DETAILED DESCRIPTION We claim: 1.
A diasteromic salt of i.
a bicyclic imino-.
alpha.
-carboxylic ester of the formulae Ia or Ib ##STR15## in which the two bridgehead hydrogen atoms have the cis configuration, the COOR group is oriented endo with respect to the bicyclic ring system, the carbon atom .
alpha.
to the COOR group has the R or S configuration, and (a) A and B.
sup.
1 denote hydrogen, and B.
sup.
2 and C together form a chain of the formula --(CH.
sub.
2).
sub.
n --, with n being 3, 4, 5, 6, or a chain of the formula --(CH.
sub.
2).
sub.
p --CH.
dbd.
CH(CH.
sub.
2).
sub.
q -- with (p+q) being, 1, 2, 3 or 4, or (b) C and B.
sup.
2 denote hydrogen, and A and B.
sup.
1 together form one of the chains defined above under (a), and (c) R represents alkyl having 1 to 6 carbon atoms, cycloalkyl having 4 to 8 carbon atoms or aralkyl having 7 to 13 carbon atoms, and ii.
an optically active R- or S- aminocarboxylic acid which contains a phenyl nucleus selected from the group consisting of R- and S-phenylalanine, R- and S-C-phenylglycine, R- and S-.
beta.
-phenyl-.
alpha.
-aminobutyric acid, R- and S-3, 4-dihydroxyphenylalanine, R- and S-.
beta.
-phenylserine and R- and S-tyrosine, the amino group of which is acylated by (C.
sub.
1 -C.
sub.
6)-alkanoyl, tert.
-butoxycarbonyl or benzyloxycarbonyl and any free hydroxy group of which can be O-alkylated by (C.
sub.
1 -C.
sub.
6)-alkyl or benzyl.
2.
A compound as claimed in claim 1, wherein the carbon atom .
alpha.
to the COOR group of the bicyclic imino-.
alpha.
-carboxylic ester has the S configuration.
3.
A compound as claimed in claim 2, wherein the bicyclic imino-.
alpha.
-carboxylic ester is an ester of cis, endo-2-azabicyclo[3.
3.
0]octane-3S-carboxylic acid.
4.
A compound as claimed in claim 3, wherein the bicyclic imino-.
alpha.
-carboxylic ester is benzyl cis, endo-2-azabicyclo[3.
3.
0]octane-3S-carboxylate.
5.
A compound as claimed in claim 2, wherein the bicyclic imino-.
alpha.
-carboxylic ester is an ester of cis, endo-octahydro[1H]indole-2S-carboxylic acid.
6.
A compound as claimed in claim 5, wherein the bicyclic imino-
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