2-(4-Nitro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester → tert-Butyl 2-(4-aminophenyl)morpholine-4-carboxylate

Participants

Reaction Steps

A mixture of 2-(4-nitro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (20 mg, 0.064 mmol) and Pd/C (5%, 2 mg) in methanol was stirred under hydrogen for 24 h. The catalyst was filtered off and washed with methanol. The filtrate was evaporated to give the title compound as an off-white solid (14 mg, 0.050 mmol, 78%). ESMS m/z 223 (M+H-tBu)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.00 (d, J=8.3 Hz, 2H) 6.52 (d, J=8.3 Hz, 2H) 5.04 (s, 2H) 4.15 (dd, J=10.5, 2.5 Hz, 1H) 3.88 (dd, J=11.8, 2.5 Hz, 1H) 3.76 (d, J=12.8 Hz, 2H) 3.48 (td, J=11.7, 2.8 Hz, 1H) 2.92 (br. s., 1H) 2.77 (br. s., 1H) 1.41 (s, 9H).

Provenance & Evidence