反应详情

To a stirred solution of methyl 4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methyloxy-3-methylbenzoate (301.6 mg, 0.863 mmol) in CH2Cl2 (6 mL) was added TFA (1.2 mL) at 0° C., and the mixture was stirred at room temp for 1 hr. The solvent was removed under a reduced pressure, and the residue was made basic by the addition of 1 N NaOH. The mixture was extracted with CHCl3. The extract was washed with brine, dried over Na2SO4, and concentrated under a reduced pressure to afford 192.5 mg (90%) methyl 3-methyl-4-(2-pyrrolidinyl)methoxybenzoate as an oil. 1H-NMR (400 MHz, CDCl3) δ 1.58–1.65 (m, 1H), 1.78–2.00 (m, 3H), 2.24 (s, 3H), 2.97 (dt, J=6.8, 10.2 Hz, 1H), 3.05 (dt, J=5.9, 6.8 Hz, H), 3.54–3.58 (m, 1H), 3.87 (s, 3H), 3.92 (dd, J=6.3, 9.3 Hz, 1H), 3.99 (dd, J=4.9, 9.3 Hz, 1H), 6.81 (d, J=8.3 Hz, 1H), 7.83 (s, 1H), 7.85 (dd, J=2.0, 8.3 Hz, 1H); MS (FAB) m/z 250 (M++1).

1. customThe solvent was removed under a reduced pressure
2. additionthe residue was made basic by the addition of 1 N NaOH
3. extractionThe mixture was extracted with CHCl3
4. washThe extract was washed with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under a reduced pressure