反应详情

8-(3-Amino-phenyl)-3-benzyl-3-aza-bicyclo[3.2.1]octan-8-ol (1.63 g, 5.28 mmol) stirred in pyridine (20 ml) at 0° C. was charged with 2-methoxy-ethanesulfonyl chloride (1.26 g, 7.93 mmol) dropwise causing a color change from yellow to bright orange. The reaction was warmed to room temperature and judged complete by TLC after 1 h. Following addition of water (20 ml), the product was extracted with EtOAc (4×30 ml), washed with saturated aqueous NaCl solution (6×30 ml), dried over Na2SO4, filtered and concentrated to a crude red oil (2.37 g, >100%). 1H NMR (400 MHz, CDCl3) δ 7.35–7.10 (m, 4H), 3.78 (ddd, J=7.5, 3.3, 2.1 Hz, 2H), 3.59 (s, 2H), 3.36 (d, J=2.5 Hz, 3H), 3.17, (m, 2H), 2.85 (d, J=16.3 Hz, 3H), 2.61 (d, J=8.3 Hz, 2H), 2.36 (s, 2H), 1.79 (d, J=7.0 Hz, 2H), 1.37 (d, J=10.0 Hz, 2H); APCI MS m/z 431.2 (M+1)+.

1. extractionthe product was extracted with EtOAc (4×30 ml)
2. washwashed with saturated aqueous NaCl solution (6×30 ml)
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated to a crude red oil (2.37 g, >100%)