Sodium Bicarbonate → 7-{2-[4-(4-Fluoro-phenyl)-3-hydroxy-butyl]-5-oxo-pyrrolidin-1-yl}heptanenitrile

To a solution of 7-{2-[3-(tert-butyl-dimethyl-silanyloxy)-4-(4-fluoro-phenyl)-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile (158 mg, 0.333 mmol) in THF (20 mL) at 0° C. was added TBAF (1M in THF, 0.50 mL, 0.50 mmol). The reaction mixture was stirred at room temperature for 3 h and saturated aqueous NaHCO3 was added. The volatiles were removed in vacuo. The remaining aqueous solution was washed with CHCl3 (4×5 mL) and the combined organic solutions were dried (MgSO4), filtered and concentrated. The residue was purified by medium pressure chromatography (1:1 hexanes:EtOAc to EtOAc) provided 7-{2-[4-(4-fluoro-phenyl)-3-hydroxy-butyl]-5-oxo-pyrrolidin-1-yl}-heptanenitrile (82 mg). 1H NMR (CDCl3) δ7.15 (m, 2H), 7.00 (m, 2H), 3.77 (m, 1H), 3.58 (m, 2H), 2.89 (m, 1H), 2.79 (m, 1H), 2.64 (m, 1H), 2.34 (m, 4H), 2.12 (m, 1H), 1.68-1.24 (m, 14H); MS 361.2 (M+1).

1. customThe volatiles were removed in vacuo
2. washThe remaining aqueous solution was washed with CHCl3 (4×5 mL)
3. dry with materialthe combined organic solutions were dried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was purified by medium pressure chromatography (1:1 hexanes:EtOAc to EtOAc)

ORD record

ord-c6c7a8d2dcbc44a5b321276e607eb5b0

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06737437B2