Reaction Steps
A suspension of 2-[(1S)-1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-7-nitro-2,3-dihydro-isoindol-1-one (3.0 g, 6.9 mmol) and Pd/C (10% 350 mg) in methanol/ethyl acetate (150 mL each) was shaken under hydrogen (50-60 psi) in a Parr for 20 hours. The suspension was filtered thru a pad of Celite, and washed with acetone (300 mL). The solvent was removed in vacuo to give a solid. The solid was slurried in methanol (10 mL) for 3 hours. The suspension was filtered and washed with methanol to give 7-amino-2-[(1S)-1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-2,3-dihydro-isoindol-1-one as a white solid (1.5 g, 55% yield): mp, 135-137° C.; 1H NMR (CDCl3) δ 1.44 (t, J=7 Hz, 3H, CH3), 2.93 (s, 3H, CH3), 3.66 (dd, J=5, 15 Hz, 1H, CHH), 3.85 (s, 3H, CH3), 4.06 (q, J=7 Hz, 2H, CH2), 4.13 (d, J=16 Hz, 1H, CHH), 4.22 (dd, J=10, 15 Hz, 1H, CHH), 4.35 (d, J=17 Hz, 1H, CHH), 5.19 (brs, 2H, NH2), 5.64 (dd, J=5, 10 Hz, 1H, NCH), 6.54 (d, J=8 Hz, 1H, Ar), 6.61 (d, J=7 Hz, 1H, Ar), 6.83 (d, J=8 Hz, 1H, Ar), 6.90-6.96 (m, 2H, Ar), 7.20 (t, J=8 Hz, 1H, Ar); 13C NMR (CDCl3) δ 14.59, 41.28, 48.01, 51.81, 55.87, 56.14, 64.48, 110.98, 111.38, 112.22, 113.41, 114.75, 119.23, 129.89, 133.08, 142.36, 146.02, 148.72, 149.45, 170.57; Anal Calcd for C20H24N2O5S: C, 59.39; H, 5.98; N, 6.93. Found: C, 59.04; H, 6.04; N, 6.74.
