Triethylamine → 3-Fluoro-1-[2-(2-methoxy-4-nitrophenoxy)ethyl]pyrrolidine

Participants

Reaction Conditions

Reaction Steps

1-(2-Bromoethoxy)-2-methoxy-4-nitrobenzene (0.2346 g, 0.8499 mmol) and 3-fluoropyrrolidine (0.3187 g, 2.5496 mmol) were combined in DMF (5 mL). Triethylamine (0.43 g, 4.2495 mmol) was added. The reaction was heated to 80° C. and stirred for 18 h. The reaction was cooled to RT and diluted with EtOAc (50 mL). The organics were washed with water (3×100 mL), dried over MgSO4, filtered and concentrated. The residue was purified by chromatatron (98:2 CH2Cl2:MeOH). The product was subjected to hydrogenation using 10% Pd/C under 1 atm of H2. The reaction was stirred for 18 h and was then filtered through celite and the celite washed with EtOAc (2×10 mL). The organics were concentrated to give 0.0442 g (0.1740 mmol, 20%) of the product. 1H NMR (CDCl3) δ 6.75 (d, 1H, J=8.4 Hz), 6.28 (s, 1H), 6.19 (d, 1H, J=8.3 Hz), 5.26-5.13 (m, 1H), 4.10 (t, 2H, J=5.7 Hz), 3.80 (s, 3H), 3.10-2.78 (m, 6H), 2.27-2.05 (m, 2H).

Provenance & Evidence