1 Ocak 2016 Dergi makalesi Açık Erişim

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

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    <subfield code="a">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.</subfield>
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    <subfield code="a">10.1016/j.tetasy.2016.04.005</subfield>
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    <subfield code="a">Synthesis and asymmetric resolution of a dopaminergic compound: 2-amino-5-methoxyindane</subfield>
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