Synthesis of β-adrenergic blockers (R)-(−)-nifenalol and (S)-(+)-sotalol via a highly efficient resolution of a bromohydrin precursor

M Kapoor, N Anand, K Ahmad, S Koul, SS Chimni…

Index: Kapoor, Munish; Anand, Naveen; Ahmad, Khursheed; Koul, Surrinder; Chimni, Swapandeep S.; Taneja, Subhash C.; Qazi, Ghulam N. Tetrahedron Asymmetry, 2005 , vol. 16, # 3 p. 717 - 725

Full Text: HTML

Citation Number: 31

Abstract

(R)-and (S)-2-bromo-1-(4-nitrophenyl) ethanol are precursors of important β-adrenergic receptor blocking drugs (R)-nifenalol and (S)-sotalol, respectively. Both were obtained in enantiomeric pure forms via a single highly efficient enzymatic transesterification reaction of (±)-2-bromo-1-(4-nitrophenyl) ethanol using immobilized lipase PS-C-II (E> 1000; concn 200g/L), while PS lipase completely failed to react. On the other hand, the hydrolytic ...