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

HRID 2273639Notes

Reaction equation

HRID 2273639 reaction equation
[S:1]([O:11][CH:12](OS(C1C=CC(C)=CC=1)(=O)=O)/[CH:13]=[CH:14]/[CH3:15])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CC1C=CC([C@@H]2C(C(O[11CH3])=O)C3N(C/C=C/C[F:50])[C@H](CC3)C2)=CC=1.NCCC1C=CC(O)=C(O)C=1>>[C:7]1([CH3:8])[CH:9]=[CH:10][C:4]([S:1]([O:11][CH2:12]/[CH:13]=[CH:14]/[CH2:15][F:50])(=[O:3])=[O:2])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 681DopamineHCID 25109914(111C)methyl (3S,5R)-8-[(E)-4-fluorobut-2-enyl]-3-(4-methylphenyl)-8-azabicyclo[3.2.1]octane-2-carboxylateHCID 131733389(e)-But-2-enediol ditosylate

Product 1

HCID 18320920(e)-1-Fluoro-4-tosyloxy-2-buteneYield 28%

Procedure

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).

Workup

  1. customThis compound was prepared
  2. customSynthesis, radiosynthesis
  3. customReaction time
  4. temperatureunder reflux
  5. custom1 h
  6. customthe purification

Sources & evidence

ORD record
ord-d99901dd87594f8a85551c4922d4611f
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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