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Title: Convenient synthesis of Carvedilol utilizing 3-(9<i style="">H</i>-carbazol-4-yloxy)-1-chloropropan-2-yl phenyl carbonate as a key intermediate
Authors: Kumar, B Anand
Ashrafuddin, Md
Rajesh, V
Parveen, Sadhika
Madhusudhan, G
Keywords: Carvedilol
3-(9H-carbazol-4-yloxy)-1-chloropropan-2-yl phenyl carbonate
3-(9H-carbazol-4-yloxy)-1-chloropropan-2-yl2-(2-methoxyphenoxy) ethylcarbamate
Impurity B
β-Adrenergic blocking agent
β-Amino alcohol
Issue Date: May-2012
Publisher: NISCAIR-CSIR, India
Abstract: Convenient synthesis of pharmaceutically important moiety Carvedilol, <b style="">1</b> (β-adrenergic blocking agent) has been reported utilizing 3-(9<i style="">H</i>-carbazol-4-yloxy)-1-chloropropan-2-yl phenyl carbonate <b style="">8</b> as a key intermediate. The synthetic scheme involves the reaction of intermediate <b style="">8</b> with 2-(2-methoxy phenoxy)­ethanamine <b style="">5</b> by using <i style="">N</i>,<i style="">N</i>-Dimethyl-4-aminopyridine (DMAP) in <i style="">N</i>,<i style="">N</i>-dimethylformamide (DMF) which yield 3-(2-(2-methoxyphenoxy)ethyl)-5-((9<i style="">H</i>-carbazol-4-yloxy)methyl)oxa­zo­lidin-2-one <b style="">7</b> <i style="">via</i> 1-(9<i style="">H</i>-carbazol-4-yloxy)-3-chloropropan-2-yl 2-(2-methoxyphenoxy)ethylcarbamate <b style="">6</b>. The resulted compound <b style="">7</b> has further been converted to the required Carvedilol and this approach could be useful for the preparation of many β-amino alcohols without formation of Impurity B.
Description: 780-784
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.51B(05) [May 2012]

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