Trifluoroacetic acid → Methyl 2-(2-pyrrolidinyl)methoxypyridine-5-carboxylate

Participants

Reaction Steps

To a stirred solution of methyl 2-[[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy]pyridine-5-carboxylate (262.5 mg, 0.870 mmol) in CH2Cl2 (5.3 mL) was added TFA (1.1 mL) at 0° C., and the resulting 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 the 1 N NaOH, and extracted with CHCl3. The extract was washed with brine, dried over Na2SO4, and concentrated under a reduced pressure to afford 173.1 mg (94%) methyl 2-[(2-pyrrolidinyl)methoxy]pyridine-5-carboxylate as a pale yellowish oil. 1H-NMR (400 MHz, CDCl3) δ 1.49–1.58 (ddt, J=6.8, 8.8 Hz, 1H), 1.72–1.87 (m, 2H), 1.90–1.99 (m, 1H), 2.92–3.05 (m, 2H), 3.50–3.57 (ddd, J=4.4,7.3, 15.1 Hz, 1H), 3.91 (s, 3H), 4.23 (dd, J=7.8, 10.7 Hz, 1H), 4.38 (dd, J=4.4, 10.7 Hz, 1H), 6.78 (d, J=8.8 Hz, 1H), 8.15 (dd, J=2.4, 8.8 Hz, 1H), 8.80 (d, J=2.4 Hz, 1H); MS (FAB) m/z 237 (M++1).

Provenance & Evidence