Ammonium Chloride → Benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)ethyl)-2-fluorophenylcarbamate

Participants

Reaction Steps

To a solution of benzyl 2-fluoro-3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitroethyl)phenylcarbamate (3.75 g, 7.39 mmol) and ammonium chloride (5.93 g, 111 mmol) in methanol (148 mL) and tetrahydrofuran (148 mL) under nitrogen was added zinc (7.25 g, 111 mmol). After 3 hr, the reaction was filtered through a pad of CELITE®, rinsed with EtOAc and MeOH. The filtrate was concentrated in vacuo. Water (40 mL) was added followed by saturated aq. NaHCO3 (to pH ˜11 by litmus paper) and extracted with EtOAc (4×50 mL). The organic layers were combined, washed with brine (40 mL), dried over MgSO4, and concentrated in vacuo to give the desired product (3.523 g, 6.35 mmol, 86% yield) as a light tan solid.

Provenance & Evidence