1 Ocak 2016 Dergi makalesi Açık Erişim

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

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  "@context": "https://schema.org/", 
  "@id": 56325, 
  "@type": "ScholarlyArticle", 
  "creator": [
    {
      "@type": "Person", 
      "name": "Akbaba, Yusuf"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Ataturk Univ, Dept Chem, Fac Sci, Erzurum, Turkey", 
      "name": "Goksu, Suleyman"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Ataturk Univ, Dept Chem, Fac Sci, Erzurum, Turkey", 
      "name": "Sahin, Ertan"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Ataturk Univ, Dept Chem, Fac Sci, Erzurum, Turkey", 
      "name": "Kilic, Hamdullah"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Ataturk Univ, Dept Chem, Fac Sci, Erzurum, Turkey", 
      "name": "Secen, Hasan"
    }
  ], 
  "datePublished": "2016-01-01", 
  "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.", 
  "headline": "Synthesis and asymmetric resolution of a dopaminergic compound: 2-amino-5-methoxyindane", 
  "identifier": 56325, 
  "image": "https://aperta.ulakbim.gov.tr/static/img/logo/aperta_logo_with_icon.svg", 
  "license": "http://www.opendefinition.org/licenses/cc-by", 
  "name": "Synthesis and asymmetric resolution of a dopaminergic compound: 2-amino-5-methoxyindane", 
  "url": "https://aperta.ulakbim.gov.tr/record/56325"
}