反应详情

To a solution of 4-(3-{2-[3-(tert-butyl-dimethyl-silanyloxy)-4-phenyl-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzoic acid methyl ester (3.37 g, 6.43 mmol) in THF (40 mL) at 0° C. was added tetra-butylammonium fluoride (1M in THF, 9.6 mL, 9.6 mmol). The reaction mixture was stirred at room temperature for 18 h and the volatiles were removed in vacuo. EtOAc was added and the organic solution was washed with saturated aqueous NaHCO3 (2×), water (1×), and brine (1×). The organic solution was dried (MgSO4), filtered and concentrated. The residue was purified by medium pressure chromatography eluting with EtOAc to yield 2.28 g of 4-{3-[2-(3-hydroxy-4-phenyl-butyl)-5-oxo-pyrrolidin-1-yl]-propyl}-benzoic acid methyl ester. 1H NMR (CDCl3) (selected peaks) δ7.91 (d, 2H), 7.32-7.15 (m, 7H), 3.86 (s, 3H), 3.75 (m, 1H), 3.63 (m, 1H), 3.54 (m, 1H), 2.94 (m, 1H), 2.78 (m, 1H), 2.61 (m, 3H); MS 410.1 (M+1).

1. customthe volatiles were removed in vacuo
2. additionEtOAc was added
3. washthe organic solution was washed with saturated aqueous NaHCO3 (2×), water (1×), and brine (1×)
4. dry with materialThe organic solution was dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by medium pressure chromatography
8. washeluting with EtOAc