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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]

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