Trifluoroacetic acid → HCID 23512385, compound

Participants

Reaction Steps

To a stirred solution of methyl 4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl ]methoxy-3-fluorobenzoate (323.0 mg, 0.914 mmol) in CH2Cl2 (6.5 mL) was added TFA (1.3 mL) at 0° C., and the mixture was stirred 1.5 hr at room temp. 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 174.8 mg (76%) methyl 3-fluoro4-(2-pyrrolidinyl)methoxybenzoate as a brownish oil. 1H-NMR (400 MHz, CDCl3) δ 1.54–1.63 (m, 1H), 1.76–2.02 (m, 3H), 2.93–3.07 (m, 2H), 3.57 (ddd, J=4.9, 6.9, 14.3 Hz, 1H), 3.89 (s, 3H), 3.97 (dd, J=6.8, 9.3 Hz, 1H), 4.04 (dd, J=5.0, 8.8 Hz, 1H), 6.98 (t, J=17.6 Hz, 1H), 7.73 (dd, J=2.0, 11.7 Hz, 1H), 7.78 (dt, J=2.0, 8.8 Hz, 1H); MS (FAB) m/z 253 (M++1).

Provenance & Evidence