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Title: | Synthesis of racemic and chiral Carvedilol starting from corresponding 5-(chloromethyl)oxazolidin-2-one |
Authors: | Kumar, B Anand Babu, K Veera Rao, Rama Koteshwar Srinivas, Kumbam Madhusudhan, G Mukkanti, K |
Keywords: | Chiral carvedilol;5-(chloromethyl) oxazolidin-2-one;Impurity B;β-adrenergic blocking agent;β-amino alcohol |
Issue Date: | Sep-2012 |
Publisher: | NISCAIR-CSIR, India |
Abstract: | The synthesis of racemic Carvedilol ((±)-1) has been achieved starting from 2-(chloromethyl) oxirane ((±)-2) in a four-step sequence. 5-(Chloromethyl) oxazolidin-2-one ((±)-3) and 5-((9H-carbazol-4-yloxy) methyl) oxazolidin-2-one ((±)-4) are intermediates. A similar sequence starting from (R)- or (S)-2-(chloromethyl)oxirane 2 give corresponding chiral 5-((9H-carbazol-4-yloxy)methyl) oxazolidin-2-one 4 followed by chiral Carvedilol 1. The synthetic sequence followed avoids the formation of impurity B (bis impurity). This approach can be useful for the preparation of pharmaceutically important moieties containing β-amino alcohols without formation of bis impurity. |
Page(s): | 1430-1435 |
URI: | http://hdl.handle.net/123456789/14648 |
ISSN: | 0975-0983(Online); 0376-4699(Print) |
Appears in Collections: | IJC-B Vol.51B(09) [September 2012] |
Files in This Item:
File | Description | Size | Format | |
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IJCB 51B(9) 1430-1435.pdf | 91.33 kB | Adobe PDF | View/Open |
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