Dopamine → (e)-1-Fluoro-4-tosyloxy-2-butene

Participants

Reaction Steps

This compound was prepared, starting from (E)-but-2-enediol ditosylate (0.50 g, 1.26 mmol), according to the procedure described by Dollé, F.; Emond, P.; Mavel, S.; Demphel, S.; Hinnen, F.; Mincheva, Z.; Saba, W.; Valette, H.; Chalon, S.; Halldin, C.; Helfenbein, J.; Legaillard, J.; Madelmont, J. C.; Deloye, J. B.; Bottlaender, M.; Guilloteau, D. Synthesis, radiosynthesis and in vivo preliminary evaluation of [11C]LBT-999, a selective radioligand for the visualisation of the dopamine transporter with PET Bioorg. Med. Chem. 2006, 14, 1115-1125. Reaction time under reflux: 1 h; the purification was performed using column chromatography (SiO2, CH2Cl2/pentane, 8/2, v/v) to give compound 55 (87 mg, 0.36 mmol) as a colourless oil. Yield 28%; Rf (SiO2, CH2Cl2/pentane, 8/2, v/v) 0.42; IR (CCl4) ν 1179, 1190, 1375, 1599 cm−1; 1H NMR (200 MHz, CDCl3) δ 2.45 (s, 3H), 4.57 (m, 2H), 4.82 (dd, 2H, 2JH-F=46.7 Hz, J=4.7 Hz), 5.85 (m, 2H), 7.36 (d, 2H, J=8.2 Hz), 7.79 (d, 2H, J=8.2 Hz).

Provenance & Evidence