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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
<span style="font-size:12.0pt;font-family: "Times New Roman";mso-fareast-font-family:"Times New Roman";mso-ansi-language: EN-GB;mso-fareast-language:EN-US;mso-bidi-language:AR-SA" lang="EN-GB">Impurity <b style="mso-bidi-font-weight:normal">B</b></span>
β-adrenergic blocking agent
β-amino alcohol
Issue Date: Sep-2012
Publisher: NISCAIR-CSIR, India
Abstract: The synthesis of racemic Carvedilol ((±)-<b>1</b>) has been achieved starting from 2-(chloromethyl) oxirane ((±)-<b>2</b>) in a four-step sequence. 5-(Chloromethyl) oxazolidin-2-one ((±)-<b>3</b>) and 5-((9<i style="mso-bidi-font-style: normal">H</i>-carbazol-4-yloxy) methyl) oxazolidin-2-one ((±)-<b>4</b>) are intermediates. A similar sequence starting from (<i style="mso-bidi-font-style: normal">R</i>)- or (<i style="mso-bidi-font-style:normal">S</i>)-2-(chloromethyl)oxirane <b>2</b> give corresponding chiral 5-((9<i style="mso-bidi-font-style:normal">H</i>-carbazol-4-yloxy)methyl) oxazolidin-2-one <b>4</b> followed by chiral Carvedilol <b>1</b>. The synthetic sequence followed avoids the formation of impurity<b style="mso-bidi-font-weight: normal"> B</b> (<i style="mso-bidi-font-style:normal">bis</i> impurity). This approach can be useful for the preparation of pharmaceutically important moieties containing β-amino alcohols without formation of <i style="mso-bidi-font-style: normal">bis</i> impurity.
Description: 1430-1435
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.51B(09) [September 2012]

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