313639-98-4Relevant academic research and scientific papers
SYNTHESIS OF (4aS,7aS)-OCTAHYDRO-1H-PYRROLO[3,4-b]PYRIDINE
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Page/Page column 35-36, (2010/09/18)
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 AIk 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 AIk 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%.
Method for the enantiomer separation of cis-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane
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, (2008/06/13)
The invention relates to a method for the enantiomer separation of cis-8-benzyl-7,9-dioxo-2,8-diazabicy-clo[4.3.0]nonane (also described below as cis-6-benzyl-5,7-dioxooctahydropyrrolo[3,4-b]pyridine or dioxopyrrolopiperidine). The invention also relates to a method for producing (1S, 6R)- and (1R, 6S)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane using the above method. The invention further relates to the (?)-2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid salts of (1S, 6R)- and (1R, 6S)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane and to a method for producing the same. Finally, the invention relate to a method for the enantiomer enrichment of (1S, 6R)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]-nonane.
