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 (−)-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.