Synthesis and Asymmetric Resolution of Substituted 2-Aminoindane and 2-Aminotetralin Derivatives

Abstract

We performed the racemic synthesis and asymmetric resolution of one 2-aminoindane and three 2-aminotertalins due to their crucial biological roles in the central nervous system (CNS). For this reason, desired (+/-)-2-aminoindane and (+/-)-2-aminotetralin derivatives were synthesized starting from appropriate reagents. While highly enantio pure (+)-39, (+)-40, and ( inverted exclamation )-40 were obtained from the reaction of racemic amines with (R)-O-acetylmandeloyl chloride followed by crystallization, hydrolysis with KOH and acidification with HCl, (S)-42 and (-)-43 were synthesized via the reaction of racemic amines with (S)-mandelic acid and hydrolysis.(c) 2023 Elsevier Ltd. All rights reserved.