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

Participants

Reaction Steps

To a stirred solution of methyl 2-[[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methyloxy]pyridine -5-carboxylate (232.3 mg, 0.691 mmol) in CH2Cl2 (4.6 mL) was added TFA (0.9 mL) at 0° C., and the reaction mixture was stirred at room temp for 2 hr. The solvent was removed under a reduced pressure and the residue was made basic by the addition of 1 N NaOH. The aqueous solution was extracted with CHCl3, washed with brine, and the dried over Na2SO4. The solvent was evaporated under a reduced pressure to afford 146.2 mg (90%) methyl 2-(2-pyrrolidinyl)methoxypyridine-5-carboxylate as an oil. 1H-NMR (400 MHz, CDCl3) δ 1.49–1.58 (m, 1H), 1.72–2.18 (m, 3H), 2.92–3.05 (m, 2H), 3.50–3.57 (m, 1H), 3.91 (s, 3H), 4.23 (dd, J=8.0, 10.7 Hz, 1H), 4.38 (dd, J=4.4, 10.3 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