Synthesis of (4as,7as)-octahydro-1h-pyrrolo[3,4-b]pyridine

Details Synthesis of (4as,7as)-octahydro-1h-pyrrolo[3,4-b]pyridine Synthesis of (4as,7as)-octahydro-1h-pyrrolo[3,4-b]pyridine

C - Chemistry, Metallurgy

07

D

C07D 211/16 (2006.01) C07D 471/04 (2006.01)

Patent

CA 2751548

The present invention relates to the stereoselective synthesis of (4aS,7aS)-octahydro-1H-pyrrolo [3, 4- b]pyridine, as well as the conversion thereof, to give Moxifloxacin. Particularly, the present invention relates to a method for the synthesis of (4aS,7aS)-octahydro-1H-pyrrolo [3, 4-b]pyridine of formula (I) comprising : (a) the optical resolution by enzymatic hydrolysis of the intermediate dialkyl-1-alkylcarbonylpiperidine-2,3-dicarboxylate racemate of formula (II) to give, following isolation, the intermediate dialkyl-(2S,3R)-1-alkylcarbonyl-piperidine-2,3-dicarboxylate of formula (III) in which Alk is a straight or branched C1-C5 alkyl group; (b) the conversion of the intermediate (III) to (4aR,7aS)-1-alkylcarbonylhexahydrofuro [3, 4-b]pyridine-5,7-dione of formula (IV) in which Alk has the meanings set forth above; (c) the conversion of the intermediate (IV) to (4aS,7as)-octahydro-1H-pyrrolo[3, 4-b]pyridine of formula (I) with an optical purity above 99%.

L'invention concerne la synthèse stéréosélective de (4aS, 7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine, ainsi que sa conversion, pour donner la moxifloxacine. En particulier, la présente invention porte sur un procédé de synthèse de la (4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridine de formule (I) comprenant : (a) la résolution optique par hydrolyse enzymatique de l'intermédiaire dialkyl-1-alkylcarbonylpipéridine-2,3-dicarboxylate racémate de formule (II) pour donner, après isolement, l'intermédiaire dialkyl-(2S,3R)-1-alkylcarbonyl-pipéridine-2,3-dicarboxylate de formule (III) dans lequel Alk est un groupe alkyle en C1-C5 à chaîne droite ou ramifiée; (b) la conversion de l'intermédiaire (III) en la (4aR,7aS)-1-alkylcarbonylhexahydrofuro[3,4-b]pyridine-5,7-dione de formule (IV) dans laquelle Alk a les significations énoncées ci-dessus; (c) la conversion de l'intermédiaire (IV) en la (4aS,7as)-octahydro-1H-pyrrolo[3,4-b]pyridine de formule (I) avec une pureté optique au-dessus de 99 %.

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