|
NISCAIR ONLINE PERIODICALS REPOSITORY (NOPR) >
NISCAIR PUBLICATIONS >
Research Journals >
Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.51B [2012] >
IJC-B Vol.51B(09) [September 2012] >
| 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 |
| CC License: |  CC Attribution-Noncommercial-No Derivative Works 2.5 India |
| ISSN: | 0975-0983(Online); 0376-4699(Print) |
| Source: | IJC-B Vol.51B(09) [September 2012]
|
|
