Trifluoroacetic acid → 3-(3-Pyrrolidinyloxy)pyridine

Participants

Reaction Steps

To 1.3 gm of 3-(1-t-butoxycarbonyl-3-pyrrolidinyloxy)-pyridine was added 10 mL of solution containing 5 mL of TFA and 5 mL of CH2Cl2 at ice-bath temperature. The reaction solution was slowly warmed to room temperature and allowed to stir 50 min at room temperature. After 50 min, solvents were removed in vacuo and the crude product was purified by flash chromatography (9:1:0.05, CHCl3:MeOH:conc. NH4OH) to obtain 120 mg (30.4% yield in two steps) of a clear oil: 1H NMR (300 MHz, CD3OD) δ8.21 (1H, d, J=2.6 Hz), 8.11 (1H, d, J=4.7 Hz), 7.38 (2H, m), 5.00 (1H, m), 3.13-2.88 (4H, m), 2.20-1.95 (2H, m); Mass spectrum (ESI) m/z 165.6 (M+H+).

Provenance & Evidence