Synthesis of β-adrenergic blockers (R)-(−)-nifenalol and (S)-(+)-sotalol via a highly efficient resolution of a bromohydrin precursor
IR@IIIM: CSIR-Indian Institute of Integrative Medicine, Jammu
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| Title |
Synthesis of β-adrenergic blockers (R)-(−)-nifenalol and (S)-(+)-sotalol via a highly efficient resolution of a bromohydrin precursor
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| Creator |
Kapoor, Munish
Anand, Naveen Ahmad, Khursheed Koul, Surrinder Chimni, Swapandeep S. Taneja, Subhash C. Qazi, Ghulam N. |
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| Subject |
Chemical Sciences
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| Description |
Abstract—(R)- and (S)-2-bromo-1-(4-nitrophenyl)ethanol are precursors of important b-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 200 g/L), while PS
lipase completely failed to react. On the other hand, the hydrolytic method also produced enantiorich precursors though relatively less efficient (PS-C-II, E = 5.1). Out of all the approaches employed the transesterification method proved to be the most efficient.
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| Date |
2005
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://iiim.csircentral.net/356/1/10.1016j.tetasy.2004.12.016.pdf
Kapoor, Munish and Anand, Naveen and Ahmad, Khursheed and Koul, Surrinder and Chimni, Swapandeep S. and Taneja, Subhash C. and Qazi, Ghulam N. (2005) Synthesis of β-adrenergic blockers (R)-(−)-nifenalol and (S)-(+)-sotalol via a highly efficient resolution of a bromohydrin precursor. Tetrahedron: Asymmetry, 16 (3). pp. 717-725. ISSN 09574166 |
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| Relation |
http://dx.doi.org/10.1016/j.tetasy.2004.12.016
http://iiim.csircentral.net/356/ |
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