Diisopropyl Ether → tert-butyl N-[(4-aminophenyl)methyl]-N-methylcarbamate

Participants

Reaction Steps

A Parr bottle was charged with (4-nitrobenzyl)-methy-carbarnic acid tert-butyl ester (30.0 g, 113 mmol), 150 mL EtOAc, and 10% Pd/C (3.0 g, 10 wt %), and shaken under 40 psi hydrogen for 90 min. When hydrogen uptake ceased, the reaction vessel was purged with nitrogen, filtered through celite, and concentrated to provide a tan solid, which was granulated with 300 mL of isopropyl ether to provide the title compound as an off-white solid (17.7 g in two crops, 75 mmol, 66% yield):

Provenance & Evidence