(2S)-2-(1-methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]-1-[2-(methylsulfonyl)-ethyl]piperazine → 4-{(3S)-3-(1-methylethyl)-4-[2-(methylsulfonyl)ethyl)-1-piperazinyl]-2-(methyloxy)aniline

Participants

Reaction Steps

(2S)-2-(1-Methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]-1-[2-(methylsulfonyl)-ethyl]piperazine (0.382 g, 0.991 mmol) was dissolved in 15 mL of EtOH with stirring. 10% Palladium on carbon (0.105 g, 0.0987 mmol) was added, and the reaction was placed under 1 atm of H2 using a balloon. The reaction was stirred for 8 h and filtered through celite washing with EtOAc. The filtrate was concentrated in vacuo to provide the title compound of step G (0.349 g, 0.982 mmol, 99%). 1H NMR (400 MHz, DMSO-d6) δ 6.47 (d, J=8.4 Hz, 1H), 6.41 (d, J=2.4 Hz, 1H), 6.25 (dd, J=8.4, 2.4 Hz, 1H), 4.17 (br. s., 2H), 3.69 (s, 3H), 3.28-3.39 (m, 1H), 3.04-3.23 (m, 4H), 2.98 (s, 3H), 2.90 (d, J=11.0 Hz, 1H), 2.70-2.81 (m, 1H), 2.48-2.58 (m, 1H), 2.30-2.44 (m, 2H), 2.16-2.25 (m, 1H), 2.02-2.15 (m, 1H), 0.91 (d, J=7.0 Hz, 3H), 0.83 (d, J=6.8 Hz, 3H).

Provenance & Evidence