(2S)-N,N-dimethyl-1-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-1-oxo-2-propanamine → 1-[(2S)-2-(dimethylamino)propanoyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine

Participants

Reaction Steps

To a solution of (2S)-N,N-dimethyl-1-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-1-oxo-2-propanamine (2.2 g, 7.50 mmol) in Ethyl acetate (250 mL) was added Pd/C (0.798 g, 0.750 mmol) and the reaction was maintained under 50 psi of H2(g) overnight on the Fisher-Porter apparatus. The reaction was filtered through a celite pad which was washed with ethyl acetate, concentrated by rotary evaporation, and high maintained under vacuum for 12 hours to afford 1-[(2S)-2-(dimethylamino)propanoyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine (1.5 g, 76%). ESIMS (M+H)+=264.

Provenance & Evidence