Concise syntheses of 2-aminoindans via indan-2-ol

Article abstract of DOI:10.1016/j.tet.2005.04.069

2-Amino-5,6-dimethoxyindan hydrochloride was synthesized in seven steps and with an overall yield of 48%. Indan-2-ol was converted to 5,6-dibromo-indan-2- ol in three steps by acetylation, electrophilic bromination and deacetylation. Dimethoxylation of 5,6-dibromoindan-2-ol with NaOCH₃ in the presence of CuI gave 5,6-dimethoxy-indan-2-ol, which was converted to 2-amino-5,6-dimethoxyindan hydrochloride by azidation, followed by Pd-C catalyzed hydrogenation. Similarly, 2-amino-5-bromoindan was synthesized in five steps and with an overall yield of 50%. Indan-2-ol was converted to 2-aminoindan by azidation followed by Pd-C catalyzed hydrogenation. The reaction of 2-aminoindan with 2.5 equiv Br₂ afforded 2-amino-5,6- dibromoindan.