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

Participants

Reaction Steps

To a solution of (2R)-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 maintained under 50 psi of H2(g) overnight on the Fisher-Porter. The crude material was filtered through a celite pad, washed with ethyl acetate, concentrated on the rotovap, and placed under high vacuum overnight to afford 1-[(2R)-2-(dimethylamino)propanoyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine (1.4 g, 71%). ESIMS (M+H)+=264.

Provenance & Evidence