4-Tert-butyl-2-cyclopentenyl-5-nitrophenyl methyl carbonate → 5-Amino-4-tert-butyl-2-cyclopentylphenyl methyl carbonate

Participants

Reaction Steps

To a flask charged with 10% Pd/C (132 mg) under inert atmosphere was added a solution of 4-tert-butyl-2-cyclopentenyl-5-nitrophenyl methyl carbonate (660 mg, 2.07 mmol) in ethanol (20 mL). The reaction was stirred under H2 atmosphere for 3 h, then filtered and dried down to provide 5-amino-4-tert-butyl-2-cyclopentylphenyl methyl carbonate as an off-white crystalline solid (556 mg, 92% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 6.97 (s, 1H), 6.38 (s, 1H), 4.81 (s, 2H), 3.80 (s, 3H), 2.84 (m, 1H), 1.87-1.80 (m, 2H), 1.72-1.66 (m, 2H), 1.62-1.56 (m, 2H), 1.47-1.39 (m, 2H), 1.32 (s, 9H).

Provenance & Evidence