1 Ocak 2016 Dergi makalesi Açık Erişim

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

Citation Style Language JSON

{
  "DOI": "10.1016/j.tetasy.2016.04.005", 
  "abstract": "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.", 
  "author": [
    {
      "family": "Akbaba", 
      "given": " Yusuf"
    }, 
    {
      "family": "Goksu", 
      "given": " Suleyman"
    }, 
    {
      "family": "Sahin", 
      "given": " Ertan"
    }, 
    {
      "family": "Kilic", 
      "given": " Hamdullah"
    }, 
    {
      "family": "Secen", 
      "given": " Hasan"
    }
  ], 
  "container_title": "TETRAHEDRON-ASYMMETRY", 
  "id": "56325", 
  "issue": "11-12", 
  "issued": {
    "date-parts": [
      [
        2016, 
        1, 
        1
      ]
    ]
  }, 
  "page": "475-479", 
  "title": "Synthesis and asymmetric resolution of a dopaminergic compound: 2-amino-5-methoxyindane", 
  "type": "article-journal", 
  "volume": "27"
}