Synthesis of the four stereoisomers of several 3‐(1‐aminoethyl)pyrrolidines. Important intermediates in the preparation of quinolone antibacterials | Zendy

Schroeder Mel C. | Zendy; Kiely John S. | Zendy; Laborde Edgardo | Zendy; Johnson Don R. | Zendy; Szotek Deedee L. | Zendy; Domagala John M. | Zendy; Stickney Thomas M. | Zendy; Michel Andre | Zendy; Kampf Jeffrey W. | Zendy

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research