73305-09-6Relevant articles and documents
Synthesis and asymmetric resolution of a dopaminergic compound: 2-amino-5-methoxyindane
Akbaba, Yusuf,G?ksu, Süleyman,?ahin, Ertan,Kili?, Hamdullah,Se?en, Hasan
, p. 475 - 479 (2016)
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 CHCl3, 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.
Synthesis method of 2-aminoindane derivative and product of 2-aminoindane derivative
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Paragraph 0075, (2017/02/24)
The invention provides a synthesis method of a 2-aminoindane derivative. According to the method, 5,6disubstituted 1-indanone is used as a staring raw material; bromination reaction is firstly performed; then, Gabriel reaction is performed; next, hydrazine hydrate is added; hydrolysis reaction is performed, and meanwhile, hydrazone is generated; finally, strong alkali is added into a high-boiling-point solvent to perform heating hydrolysis; the target product of the 2-aminoindane derivative is prepared. The invention also provides the 2-aminoindane derivative prepared by the synthesis method. Compared with the synthesis method of the 2-aminoindane derivative in the prior art, the synthesis method provided by the invention has the advantages that the reaction raw materials are cheap; the reaction condition is mild; the reaction steps are simple; the operation is easy; the yield of the obtained product is higher; the synthesis method is suitable for industrial production. Therefore good application prospects and market potentials are realized.
Design and synthesis of indane-ureido-thioisobutyric acids: A novel class of PPARα agonists
Matthews, Jay M.,Chen, Xiaoli,Cryan, Ellen,Hlasta, Dennis J.,Rybczynski, Philip J.,Strauss, Kim,Tang, Yuting,Xu, June Z.,Yang, Maria,Zhou, Lubing,Demarest, Keith T.
, p. 6773 - 6778 (2008/09/17)
A series of aminoindane derivatives were synthesized and shown to be potent PPARα agonists. The compounds were obtained as racemates in 12 steps, and tested for PPARα activation and PPARα mediated induction of the HD gene. SAR was developed by variation to the core structure as shown within. Oral bioavailability was demonstrated in a Sprague-Dawley rat, while efficacy to reduce plasma triglycerides and plasma glucose was demonstrated in db/db mice.
