L-Proline → 1-[5-Fluoro-7-(methylsulfonyl)-4H-1,3-benzodioxin-2-YL]-N-methylmethanamine

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Reaction Steps

Preparation according to Example 17 with a small alteration, no base used. 1-(7-bromo-5-fluoro-4H-1,3-benzodioxin-2-yl)-N-methylmethanamine (0.33 g, 1.2 mmol), sodium methanesulfinate (0.18 g, 1.49 mmol, 85%), copperiodide (23 mg, 0.12 mmol), L-proline (69 mg, 0.60 mmol) and DMSO (6.0 ml) was heated at 140° C. for 45 min. Purification by flash column chromatography (EtOAc/MeOH 4:1) afforded the title compound (30 mg, 10%). The amine was converted into the hydrochloric acid salt and crystallized from MeOH/EtOH/DEE. The crystals were washed thoroughly with DEE. M.p. 234° C. 1H-NMR (400 MHz, MeOH): δ 7.28 (2H, m), δ 5.26 (1H, t, J 4.8 Hz), δ 5.05 (2H, dd, J1 20.4 Hz, J2 16.0 Hz), δ 3.13 (3H, s), δ 2.95 (2H, m), δ 2.47 (3H, s).

Provenance & Evidence