tert-Butyl 4-(4-nitrophenyl)-1,4-diazepane-1-carboxylate → Tert-butyl 4-(4-aminophenyl)-1,4-diazepane-1-carboxylate

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Reaction Steps

4-(4-Nitro-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (3.6 g) was diluted with ethanol (50 mL) and 10% Pd/C (400 mg) was added. The mixture was placed on a Parr shaker for hydrogenation at 50 psi for 3 hr The mixture was filtered and the solvent was removed to afford 4-(4-amino-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (3.2 g, 99% yield) as amorphous purple semi-solid. ES-MS for C16H25N3O2 calcd. (m/e) 291, observed 292 (M+H).

Provenance & Evidence