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Synthesis of the four stereoisomers of several 3‐(1‐aminoethyl)pyrrolidines. Important intermediates in the preparation of quinolone antibacterials
Author(s) -
Schroeder Mel C.,
Kiely John S.,
Laborde Edgardo,
Johnson Don R.,
Szotek Deedee L.,
Domagala John M.,
Stickney Thomas M.,
Michel Andre,
Kampf Jeffrey W.
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290620
Subject(s) - chemistry , diastereomer , ketone , oxime , stereochemistry , stereoselectivity , pyrrolidinones , quinolone , combinatorial chemistry , organic chemistry , antibiotics , catalysis , biochemistry
The 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.