L-Proline → N-{[6-Fluoro-7-(methylsulfonyl)-4H-1,3-benzodioxin-2-YL]methyl}propan-1-amine

Participants

Reaction Steps

Preparation according to Example 18. N-[(7-bromo-6-fluoro-4H-1,3-benzodioxin-2-yl)methyl]propan-1-amine (0.30 g, 0.99 mmol), sodium methanesulfinate (0.15 g, 1.23 mmol, 85%), copperiodide (19 mg, 0.10 mmol), L-proline (56 mg, 0.49 mmol) and DMSO (6 ml) was heated at 140° C. for 1 h. Purification was made twice by flash column chromatography (ETOAc/MeOH 10:1) and afforded the title compound (135 mg, 45%). The amine was converted into the hydrochloric acid salt and crystallized from EtOH/DEE. M.p. 225° C. 1H-NMR (400 MHz, MeOH): δ 7.34 (1H, d, J 6.0 Hz), δ 7.13 (1H, d, J 9.6 Hz), δ 5.21 (1H, t, J 4.8 Hz), δ 5.02 (2H, dd, J1 45.2 Hz, J2 15.6 Hz), δ 3.23 (3H, s), δ 2.96 (2H, m), δ 2.64 (2H, t, J 7.6 Hz), δ 1.56 (2H, m), δ 0.95 (3H, t, J 7.2 Hz).

Provenance & Evidence