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Synthesis of the four stereoisomers of several 3‐(1‐aminoethyl)pyrrolidines. Important intermediates in the preparation of quinolone antibacterials
dc.contributor.authorSchroeder, Mel C.en_US
dc.contributor.authorKiely, John S.en_US
dc.contributor.authorLaborde, Edgardoen_US
dc.contributor.authorJohnson, Don R.en_US
dc.contributor.authorSzotek, Deedee L.en_US
dc.contributor.authorDomagala, John M.en_US
dc.contributor.authorStickney, Thomas M.en_US
dc.contributor.authorMichel, Andreen_US
dc.contributor.authorKampf, Jeffrey W.en_US
dc.date.accessioned2013-02-12T19:00:37Z
dc.date.available2013-02-12T19:00:37Z
dc.date.issued1992-10en_US
dc.identifier.citationSchroeder, Mel C.; Kiely, John S.; Laborde, Edgardo; Johnson, Don R.; Szotek, Deedee L.; Domagala, John M.; Stickney, Thomas M.; Michel, Andre; Kampf, Jeffrey W. (1992). "Synthesis of the four stereoisomers of several 3‐(1‐aminoethyl)pyrrolidines. Important intermediates in the preparation of quinolone antibacterials." Journal of Heterocyclic Chemistry 29(6): 1481-1498. <http://hdl.handle.net/2027.42/96292>en_US
dc.identifier.issn0022-152Xen_US
dc.identifier.issn1943-5193en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/96292
dc.description.abstractThe use of S ‐α‐methylbenzyl as a chiral auxiliary at N 1 allowed separation of diastereomeric 2‐pyrrolidinones substituted with an ester, ketoester, ketone and oxime at the C 4 position. Reduction of each diastereomer of 4‐[1‐(hydroxyimino)ethyl]‐1‐(1‐phenylethyl)‐2‐pyrrolidinone, 10s and 10r , provided a pair of epimeric amines, [ 11sr and 11ss ] and [ 11rs and 11rr ], that were separated by chromatography. The four stereoisomers of 4‐(1‐aminoethyl)‐1‐(1‐phenylethyl)‐2‐pyrrolidinone, 11 , were elaborated into several stereochemically pure 3‐(1‐aminoethyl)pyrrolidines, 1 and 15‐23 . These compounds are useful intermediates (C 7 side chains) for quinolone antibacterials.en_US
dc.publisherWiley‐Blackwellen_US
dc.titleSynthesis of the four stereoisomers of several 3‐(1‐aminoethyl)pyrrolidines. Important intermediates in the preparation of quinolone antibacterialsen_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelOrganic Chemistryen_US
dc.subject.hlbtoplevelScienceen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumUniversity of Michigan, Department of Chemistry, Ann Arbor, Michiganen_US
dc.contributor.affiliationotherChemistry Department, Parke‐Davis Pharmaceutical Research Division/Warner Lambert Co. Ann Arbor, Michigan 48105‐1047en_US
dc.contributor.affiliationotherUniversity of Sherbrooke, Department of Chemistry, Sherbrooke, Quebec, Canadaen_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/96292/1/5570290620_ftp.pdf
dc.identifier.doi10.1002/jhet.5570290620en_US
dc.identifier.sourceJournal of Heterocyclic Chemistryen_US
dc.identifier.citedreferenceI. Hayakawa and S. Atarashi, Daiichi Seiyaka Co. Ltd.,European Patent Application 0 207 420 A2( 1986 ); Chem. Abstr., 106, 138267f ( 1987 ).en_US
dc.identifier.citedreferenceJ. P. Sanchez, J. M. Domagala, S. E. Hagan, C. L. Heifetz, M. P. Hutt and J. B. Nichols, J. Med. Chem., 31, 983 ( 1988 ).en_US
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dc.identifier.citedreferenceInternational Tables for X‐ray Crystallography,Vol IV, Kynoch, Birmingham, England, 1974.en_US
dc.identifier.citedreferenceE. J. Gabe, F. L. Lee and Y. LePage, The NCRVAX Crystal Structure System.In Crystallographic Computing 3, G. M. Sheldrick, C. Krüger and R. Goddard, ed, Oxford Clarendon Press, 1985,pp 167 – 174.en_US
dc.identifier.citedreferenceJ. M. Domagala, M. Cohen, J. Kiely, S. Hagen, E. Laborde, M. Schroeder, J. Sesnie and M. J. Suto,Interscience Conference on Antimicrobial Agents and Chemotherapy, 1991,Chicago, IL, Poster 1439.en_US
dc.identifier.citedreferenceCrystallographic data was obtained by Dr. Jeffrey W. Kempf and has been submitted to the Cambridge Crystallographic Databank.en_US
dc.identifier.citedreferenceA more satisfactory analysis for hydrogen in compound 22sr could not be obtained, however, purification by coupling to a quinolone substrate as for compound lss gave the desired product with satisfactory analytical and spectral data.en_US
dc.identifier.citedreferencea T. P. Mawhinney and M. A. Madson, J. Org. Chem., 47, 3336 ( 1982 ); bPierce Handbook and General Catalog, 1989,p 154.en_US
dc.identifier.citedreferenceCrystallographic data was obtained by Dr. Andre Michel and has been submitted to the Cambridge Crystallographic Databank.en_US
dc.identifier.citedreferencea R. B. Herbert, E. Knagg, H. M. Organ, V. Pasupathy and D. S. Towlson, Heterocycles, 25, 409 ( 1987 ); b D. W. Brooks, L. D. L. Lu and S. Masamune, Angew. Chem., Int. Ed. Engl., 18, 72 ( 1979 ).en_US
dc.identifier.citedreferenceT. P. Culbertson, J. M. Domagala, J. B. Nichols, S. Priebe and R. W. Skeean, J. Med. Chem., 30, 1711 ( 1987 ).en_US
dc.identifier.citedreferenceThe chiral descriptors specify stereochemistry of the C 4 and C 1 centers. For simplification the (s) descriptor for the chiral auxiliary was left off all compound numbers representing compounds containing the chiral auxiliary.en_US
dc.identifier.citedreferenceY. Kimura, K. Sato, S. Atarashi, I. Hayakawa, M. Sato and Y. Osada,Interscience Conference on Antimicrobial Agents and Chemotheraphy, 1989, Houston, TX, Poster 1192.en_US
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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