Water → 1-(Tert-butoxycarbonyl)-2-[2-(4-ethoxycarbonylphenyl)ethynyl]pyrrolidine

Participants

Reaction Steps

A suspension of ethyl 4-iodobenzoate (1.7 mL, 10 mmol), Pd(PPh3)4 (578 mg, 0.5 mmol), and CuI (190 mmol, 1 mmol) in i-Pr2NH (20 mL) was stirred for 0.5 hr under N2. To this mixture was added a solution of 1-(tert-butoxycarbonyl)-2-ethynylpyrrolidine (1.95 g, 10 mmol) in i-Pr2NH (20 mL) for over 10 min. After stirring for 3 hr at room temp, the mixture was poured into H2O and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, and evaporated. The residue was chromatographed on silica-gel with n-hexane-AcOEt (10:1, v/v) as eluent to give 2.77 g (81%) 1-(tert-butyloxycarbonyl)-2-(2-(4-ethoxycarbonylphenyl)ethynyl) pyrrolidine as a colorless oil. 1H-NMR (CDCl3) δ 1.37 (3 H, t, J=6.8 Hz), 1.49 (9 H, s), 1.85–2.12 (4 H, m), 3.37–3.51 (2 H, m), 4.37 (2 H, q, J=6.8 Hz), 4.54–4.77 (1 H, m), 7.44 (2 H, d, J=7.8 Hz), 7.96 (2 H, d, J=7.8 Hz)

Provenance & Evidence