Ethyl formate → 3-Amino-2,3-dihydro-1H-inden-5-ol

Participants

Reaction Steps

N-Methyl-6-hydroxy-1-aminoindan was prepared by demethylation of 6-methoxy-N-methyl-1-aminoindan, which was prepared from 6-methoxy-1-aminoindan by reductive alkylation (e.g. ethyl formate, followed by LiAlH4 reduction), or alternatively, by reductive amination (MeNH2, HCl, NaCNBH3) of 6-methoxy-1-indanone2. N-ethyl-6-hydroxy-1-aminoindan was obtained by acetylation of 6-hydroxy-1-aminoindan (Ac2O, KOH), followed by reduction (LiAH4). N,N-Dimethyl-6-hydroxy-1-aminoindan was prepared by demethylation of the corresponding 6-methoxy analogue, which was prepared by reductive alkylation (formaldehyde, formic acid) of 6-methoxy-1-aminoindan. 4-Hydroxy-1-aminoindan may be prepared from 4-hydroxy indanone by converting the latter to the oxime, followed by reduction1. 4-Hydroxy indanone may be prepared from dihydrocoumarin.3

Provenance & Evidence