C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][CH:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]2=[O:26])=[C:11]([N+:27]([O-])=O)[CH:10]=1)C1C=CC=CC=1.C1COCC1.[H][H]>CCO.[Pd]>[NH2:27][C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][C:12]=1[N:15]1[CH2:19][CH2:18][CH:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]1=[O:26]Ethyl 2-(1-(4-(benzyloxy)-2-nitrophenyl)-2-oxopyrrolidin-3-yl)acetate (1.09 g, 2.73 mmol) was taken up in EtOH and THF (1:1 mixture, 40 mL) and Pd/C (500 mg) was added. The reaction was pressurized with hydrogen (500 psi) in a bomb reactor and stirred at room temperature for 1 h. The reaction mixture was filtered through a pad of Celite® and the filtrate was concentrated under reduced pressure to provide the title compound (752 mg). LCMS m/z=279.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.27 (t, J=7.1 Hz, 3H), 1.96-2.08 (m, 1H), 2.38-2.48 (m, 1H), 2.70 (dd, J=16.9, 7.7 Hz, 1H), 2.86 (dd, J=17.0, 4.0 Hz, 1H), 2.95-3.05 (m, 1H), 3.63-3.79 (m, 2H), 4.18 (q, J=7.2 Hz, 2H), 6.53 (d, J=2.7 Hz, 1H), 6.59 (dd, J=8.6, 2.6 Hz, 1H), 6.66 (d, J=8.6 Hz, 1H).
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