1 Ocak 2016 Dergi makalesi Açık Erişim

Akbaba, Yusuf; Goksu, Suleyman; Sahin, Ertan; Kilic, Hamdullah; Secen, Hasan

Dublin Core

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  <dc:creator>Akbaba, Yusuf</dc:creator>
  <dc:creator>Goksu, Suleyman</dc:creator>
  <dc:creator>Sahin, Ertan</dc:creator>
  <dc:creator>Kilic, Hamdullah</dc:creator>
  <dc:creator>Secen, Hasan</dc:creator>
  <dc:date>2016-01-01</dc:date>
  <dc:description>The racemic synthesis and subsequent resolution of 2-amino-5-methoxyindane enantiomers were achieved starting from 5-bromoindan-2-ol in six steps with 38% total yield. The first step involved the substitution of the Br atom by using NaOMe in the presence of CuI to afford 5-methoxyindan-2-ol. The OH group of 5-methoxyindan-2-ol was converted into its mesylate ester, which was converted into the corresponding azide by reaction with sodium azide. The Pd C-catalyzed hydrogenation of the azide functional group in the presence of CHCI3, followed by neutralization of the amine hydrochloride salt with NaOH, furnished the rac-2-amino-5-methoxyindane. Next, rac-2-amino-5-methoxyindane was converted into its diastereomeric amide derivatives by reaction with (R)-mandeloyl chloride. The diastereomeric amide mixture was separated by recrystallization to give the (R,S)- and (R,R)-diastereomers. The absolute configuration of the (R,S)-isomer was determined by X-ray crystallography. The hydrolysis of these diastereomers gave (R)- and (S)-2-amino-5-methoxyindane with high enantiopurity. (C) 2016 Elsevier Ltd. All rights reserved.</dc:description>
  <dc:identifier>https://aperta.ulakbim.gov.trrecord/56325</dc:identifier>
  <dc:identifier>oai:zenodo.org:56325</dc:identifier>
  <dc:rights>info:eu-repo/semantics/openAccess</dc:rights>
  <dc:rights>http://www.opendefinition.org/licenses/cc-by</dc:rights>
  <dc:source>TETRAHEDRON-ASYMMETRY 27(11-12) 475-479</dc:source>
  <dc:title>Synthesis and asymmetric resolution of a dopaminergic compound: 2-amino-5-methoxyindane</dc:title>
  <dc:type>info:eu-repo/semantics/article</dc:type>
  <dc:type>publication-article</dc:type>
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