Hydrazine → ethyl N-{4-[(5-amino-1H-indol-1-yl)methyl]benzoyl}phenylalaninate

Participants

Reaction Steps

A large excess of Raney® nickel was added in portions to a stirred solution of ethyl N-{4-[(5-nitro-1H-indol-1-yl)methyl]benzoyl}-L-phenylalaninate (2.36 g, 5 mmol), and hydrazine (1.2 mL, 38 mmol) in 100 mL of ethanol and 15 mL of THF. After stirring at room temperature for 2 h the catalyst was then removed by filtering through a short pad of Celite®521. The filtrate was concentrated to give ethyl N-{4-[(5-amino-1H-indol-1-yl)methyl]benzoyl}phenylalaninate as an off-white solid: MS (ESI) m/z 442.

Provenance & Evidence