Chemical and Pharmaceutical Bulletin p. 2157 - 2160 (1994)
Update date:2022-07-30
Topics:
Morita
Ohtsubo
Matsubara
Ohtani
Uchida
Kido
Shimizu
The enantiomers of 7-fluoro-1-methyl-3-(methylsulfinyl)-4(1H)-quinolinone [(+)-1, flosequinan], a new drug for the treatment of heart failure, were synthesized from the optically active (R)-α-methylbenzylamine derivatives of quinoline. The key intermediates, (R)-α-methylbenzylamine derivatives, were prepared by diastereomeric separation. The configuration of (+)-1 was assigned on the basis of an X-ray crystallographic analysis of the synthetic precursor (4a). The absolute configuration was found to be (R)-(+)-1 and (S)-(-)-1.
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