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IJC-B Vol.51B [2012] >
IJC-B Vol.51B(05) [May 2012] >

Title: Convenient synthesis of Carvedilol utilizing 3-(9H-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, 1 (β-adrenergic blocking agent) has been reported utilizing 3-(9H-carbazol-4-yloxy)-1-chloropropan-2-yl phenyl carbonate 8 as a key intermediate. The synthetic scheme involves the reaction of intermediate 8 with 2-(2-methoxy phenoxy)­ethanamine 5 by using N,N-Dimethyl-4-aminopyridine (DMAP) in N,N-dimethylformamide (DMF) which yield 3-(2-(2-methoxyphenoxy)ethyl)-5-((9H-carbazol-4-yloxy)methyl)oxa­zo­lidin-2-one 7 via 1-(9H-carbazol-4-yloxy)-3-chloropropan-2-yl 2-(2-methoxyphenoxy)ethylcarbamate 6. The resulted compound 7 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.
Page(s): 780-784
CC License:  CC Attribution-Noncommercial-No Derivative Works 2.5 India
ISSN: 0975-0983(Online); 0376-4699(Print)
Source:IJC-B Vol.51B(05) [May 2012]

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