Please use this identifier to cite or link to this item: http://nopr.niscair.res.in/handle/123456789/13222
Title: <span style="font-size:12.0pt;font-family: "Times New Roman","serif";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">Direct conversion of (<i style="mso-bidi-font-style:normal">R</i>)-epichlorohydrin to (<i style="mso-bidi-font-style:normal">S</i>)-3-aminopropane-1,2-diol: An important chiral C-3 building block</span>
Authors: Bhavani, Ch
Babu, K Chandra
Naresh, E
Sridhar, P
Madhusudhan, G
Keywords: <span style="font-size:12.0pt;mso-bidi-font-size: 10.0pt;font-family:"Times New Roman","serif";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">(<i style="mso-bidi-font-style:normal">S</i>)-3-Aminopropane-1,2-diol</span>
<span style="font-size:12.0pt;mso-bidi-font-size: 10.0pt;font-family:"Times New Roman","serif";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">(<i style="mso-bidi-font-style:normal">R</i>)-epichlorohydrin</span>
Azidation
Rivaroxaban (Bay-59-7939)
<img src='/image/spc_char/beta.gif' border=0>-amino alcohol
Issue Date: Dec-2011
Publisher: NISCAIR-CSIR, India
Abstract: A new and effective method for the preparation of optically active (<i style="mso-bidi-font-style:normal">S</i>)-3-amino-1,2-propanediol <b style="mso-bidi-font-weight:normal">1</b> has been established starting from (<i style="mso-bidi-font-style:normal">R</i>)-epichlorohydrin <b style="mso-bidi-font-weight:normal">2</b>. The synthetic approach involves the reaction of (<i style="mso-bidi-font-style:normal">R</i>)-epichlorohydrin <b style="mso-bidi-font-weight:normal">2</b> with acetone catalyzed by boron trifluoride etherate (BF<sub>3</sub>·OEt<sub>2</sub>) to give the (<i style="mso-bidi-font-style:normal">R</i>)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane, <b style="mso-bidi-font-weight:normal">5</b>. Replacing the chloro group in (<i style="mso-bidi-font-style:normal">R</i>)-<b style="mso-bidi-font-weight:normal">5</b> with amino group by azidation followed by reduction gives ((<i style="mso-bidi-font-style:normal">S</i>)-2,2-dimethyl-1,3-dioxolan-4-yl)methanamine <b style="mso-bidi-font-weight:normal">7</b>. Acetal deprotection of the obtained (<i style="mso-bidi-font-style:normal">S</i>)-<b style="mso-bidi-font-weight: normal">7</b> with MeOH.HCl gives (<i style="mso-bidi-font-style:normal">S</i>)-3-aminopropane-1,2-diol·HCl.
Description: 1807-1811
URI: http://hdl.handle.net/123456789/13222
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.50B(12) December 2011]

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