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Typical Procedure (Synthesis of 5c).
A solution of 4b (292 mg, 1.0 mmol) and ammonium acetate (385 mg, 5.0 mmol) in glacial acetic acid (5 mL) was refluxed for 20 h. The mixture was cooled to 20 °C and EtOAc was added. The organic layer was neutralized by repeated washing with a sat. aq solution of NaHCO3. The aqueous layer was extracted with EtOAc (3 ×) and the combined organic layers were dried (Na2SO4), filtered and the filtrate was concentrated in vacuo to give 5c as a colorless solid (280 mg, 96%) without the need of further purification; mp 103 °C, R
f
= 0.25 (hexane-EtOAc = 4:1). 1H NMR (300 MHz, CDCl3): δ = 3.75 (s, 3 H, OCH3), 3.89 (s, 3 H, OCH3), 5.30 (s, 2 H, CH2Ph), 5.44 (s, 1 H, CH), 7.37 (m, 5 H, Ph), 8.48 (br s, 1 H, NH). 13C NMR (75 MHz, CDCl3): δ = 51.63, 59.36 (OCH3), 74.17 (CH2Ph), 92.60 (CH), 127.35 (C), 128.56, 128.57, 128.73 (CH, Ph), 136.02, 144.36, 144.50 (C), 166.25, 167.35 (C=O). MS (EI, 70 eV): m/z (%) = 289 (6) [M]+, 261 (3), 170 (3), 109 (5), 91 (100). The exact molecular mass for C15H15NO5: m/z = 289.0950 ± 2 ppm was confirmed by HRMS (EI, 70 eV). IR (KBr): 3401 (br, w), 3332 (s), 3263 (w), 3257 (w), 3036 (w), 3003 (w), 2953 (m), 2928 (w), 2859 (w), 1733 (s), 1702 (s), 1674 (s), 1451 (s), 1414 (w) cm-1. Anal. Calcd for C15H15NO5 (289.28): C, 62.28; H, 5.23; N, 4.84. Found: C, 62.74; H, 5.71; N, 4.38. All new compounds gave satisfactory spectroscopic and correct analytical and/or high resolution mass data.