Trifluoroacetic acid → Methyl 3-methyl-4-(2-pyrrolidinyl)methoxybenzoate

Participants

Reaction Steps

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 mix 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 1N 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) δ1.58-1.65 (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, 1H), 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).

Provenance & Evidence