反应详情

To a solution of (+/−)-benzyl 3-(tert-butoxycarbonylamino)-4-hydroxypiperidine-1-carboxylate in dichloromethane (0.1 M solution) was added Dess-Martin periodinane (1.5 equiv.). The reaction mixture was stirred at room temperature for 16 h. Then, the saturated NaHCO3 and 0.1 N Na2S2O3 aqueous solutions were added to the reaction mixture, which was stirred for 30 min and worked up with ethyl acetate. The crude benzyl 3-(tert-butoxycarbonylamino)-4-oxopiperidine-1-carboxylate was purified by flash chromatography (30% EtOAc in hexanes, 70%). LCMS (m/z): 249.2 (MH+); LC Rt=3.98 min. 1H NMR (CDCl3): 1.41 (1H, s), 2.1-2.59 (1H, m), 2.73 (1H, m), 3.09 (1H, m), 4.30 (1H, m), 4.52 (1H, m), 4.90 (1H, m), 5.19 (2H, m), 5.45 (1H, m), 7.39 (5H, m).

1. stirringwas stirred for 30 min
2. customThe crude benzyl 3-(tert-butoxycarbonylamino)-4-oxopiperidine-1-carboxylate was purified by flash chromatography (30% EtOAc in hexanes, 70%)