An Insight into the Asymmetric Resolution of 1-Aminoindane Derivatives

Akincioglu A., AKBABA Y., Kose L. P., GÖKSU S.

CHEMISTRYSELECT, cilt.8, sa.17, 2023 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 8 Sayı: 17
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1002/slct.202300278
  • Dergi Adı: CHEMISTRYSELECT
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Anahtar Kelimeler: 1-aminoindane, asymmetric resolution, diastereomers, enantio-pure, O-acetylmandeloyl chloride, CARBONIC-ANHYDRASE INHIBITORS, RASAGILINE, DOPAMINE, DESIGN
  • Atatürk Üniversitesi Adresli: Evet

Özet

Compounds with 1-aminoindane motif exhibit vital biological activities in the central nervous system. Therefore, it is very important to synthesize new compounds with this moiety and to obtain them in high enantiopurity. In this study, novel substituted 1-aminoindane derivatives were synthesized, and their asymmetric resolutions were carried out. Accordingly, the reduction of 1-indanones with NaBH4, conversion of alcohols to azides via an alternative Mitsunobu reaction followed by reduction of azides afforded (+/-)-1-aminoindane hydrochloride or hydrobromide salts. Amine salts were converted into their free amines by using excess amount of Et3N and then in situ occurred free (+/-)-amines were reacted with (R)-O-acetylmandeloyl chloride to give diastereomeric mixtures. The crystallization of the diastereomeric mixtures followed by hydrolysis yielded the corresponding asymmetric amines with high enantio-purity.