反应详情

To a mixture of (6-oxopiperidin-2-yl)methyl methanesulfonate (0.44 g, 2.2 mmol) in DMF (15 ml) was added Cs2CO3 (3.5 g, 11 mmol) and phenol (Intermediate I) (0.88 g, 3.3 mmol). The reaction mixture was stirred at room temperature for 40 hours and partitioned between water and ethyl acetate. Organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (20% MeOH-EtOAc) gave tert-butyl ((3R)-3-hydroxy-3-(3-((6-oxopiperidin-2-yl)methoxy)phenyl)propyl)carbamate as a yellow oil. Yield (0.17 g, 20%); 1H NMR (400 MHz, CD3OD) δ 7.24 (t, J=8.0 Hz, 1H), 6.97-6.93 (m, 2H), 6.84 (d, J=8.0 Hz, 1H), 4.64 (t, J=7.2 Hz, 1H), 4.06-4.02 (m, 1H), 3.94-3.90 (m, 1H), 3.86-3.76 (m, 1H), 3.15-3.06 (m, 2H), 2.37-2.30 (m, 2H), 2.05-1.92 (m, 3H), 1.86-1.75 (m, 3H), 1.43 (s, 9H).

1. custompartitioned between water and ethyl acetate
2. washOrganic layer was washed with brine
3. dry with materialdried over anhydrous Na2SO4
4. concentrationconcentrated under reduced pressure
5. customPurification by flash chromatography (20% MeOH-EtOAc)