C - Chemistry – Metallurgy – 12 – P
Patent
C - Chemistry, Metallurgy
12
P
C12P 41/00 (2006.01) C07D 471/04 (2006.01) C12P 17/18 (2006.01)
Patent
CA 2300119
Cis- and trans-pyrrolopiperidines are advantageously separated into their optical isomers when monoacylating by enzymatic process a mixture containing (R,R)- and (S,S)-pyrrolopiperidine or (S,R)- and (R,S)-pyrrolopiperidine, thereby obtaining a mixture (I) containing (R,R)- and (S,S)-6-acyl- pyrrolopiperidine or (S,R)- and (R,S)-6-acyl-pyrrolopiperidine. Said mixture (I) is then again acylated by enzymatic process, thereby obtaining a mixture (II) containing (S,S)-1,6-diacyl- and (R,R)-6-acyl-pyrrolopiperidine or (S,R)- 1,6-diacyl- and (R,S)-6-acyl-pyrrolopiperidine; the enzyme and optionally the solvent and the excess acylating agent are then separated from the mixture (II), and the rest is treated with an aqueous acid and the (S,S)-1,6-diacyl- pyrrolopiperidine or the (S,R)-1,6-diacyl-pyrrolopiperidine is separated by extraction and the extraction residue is alkalinized, and the (R,R)-6-acyl- pyrrolopiperidine or the (R,S)-6-acyl-pyrrolopiperidine is separated by extraction. From these acylated isomer-free derivatives, the free base can optionally be prepared according to the usual methods for separating acylated groups.
Des cis- et trans-pyrrolopipéridines sont séparées de manière avantageuse en leurs isomères optiques lorsque l'on monoacyle par voie enzymatique un mélange contenant de la (R,R)- et (S,S)-pyrrolopipéridine ou bien de la (S,R)- et (R,S)-pyrrolopipéridine. On obtient alors un mélange (I) contenant de la (R,R)- et (S,S)-6-acyl-pyrrolopipéridine ou bien de la (S,R)- et (R,S)-6-acyl-pyrrolopipéridine, on acyle à nouveau par voie enzymatique ce mélange (I), on obtient alors un mélange (II) contenant de la (S,S)-1,6-diacyl- et (R,R)-6-acyl-pyrrolopipéridine ou bien de la (S,R)-1,6-diacyl- et (R,S)-6-acyl-pyrrolopipéridine, on sépare du mélange (II) l'enzyme et éventuellement le solvant et l'agent d'acylation en excès, on traite le reste avec un acide aqueux et on sépare par extraction la (S,S)-1,6-diacyl-pyrrolopipéridine ou bien la (S,R)-1,6-diacyl-pyrrolopipéridine et on alcalinise le résidu de l'extraction, et on sépare par extraction la (R,R)-6-acyl-pyrrolopipéridine ou bien la (R,S)-6-acyl-pyrrolopipéridine. A partir des dérivés acylés exempts d'isomères, on peut éventuellement préparer la base libre selon les méthodes habituelles de la séparation des groupes acylés.
Aktiengesellschaft Bayer
Fetherstonhaugh & Co.
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