Trifluoroacetic acid → 2-(2-(4-Ethoxycarbonylphenyl)ethynyl)pyrrolidine

Participants

Reaction Steps

To a stirred solution of 1-(tert-butoxycarbonyl)-2-[2-(4-ethoxycarbonylphenyl)ethynyl]pyrrolidine (2.75 g, 8 mmol) in CH2Cl2 (5 ml) was added TFA (5 mL), and the resulting mixture was stirred overnight. The mixture was concentrated in vacuo and made basic with sat. NaHCO3 and extracted with CHCl3. The extract was washed with brine, dried over MgSO4, evaporated to give 1.95 g (q.y.) 2-[2-(4-ethoxycarbonylphenyl)ethynyl]pyrrolidine as a light yellow oil. 1H-NMR (CDCl3) δ1.38 (3 H, t, J=6.8 Hz), 1.82-2.16 (4 H, m), 3.01-3.48 (2 H, m), 4.00-4.11 (1 H, m), 4.37 (2H, q, J=6.8 Hz), 4.54-4.77 (1 H, m), 7.44-7.46 (2 H, m), 7.95-7.97 (2 H, m).

Provenance & Evidence