Acetic Acid → N-{[7-(Methylsulfonyl)-4H-1,3-benzodioxin-2-YL]methyl}propan-1-amine

Participants

Reaction Steps

Preparation according to Example 4. (+)-N-benzyl-N-{[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methyl}propan-1-amine (0.21 g, 0.56 mmol), palladium on carbon (10%, 25 mg), concentrated AcOH (0.1 ml) and EtOH (10 ml) was hydrogenated at 40 psi for 1 h 15 min. Purification afforded the title compound (0.14 g, 83%, >95% e.e.) The amine was converted into the hydrochloric acid salt and crystallized from EtOH/MeOH/DEE. M.p. 235° C. [α]DMeOH=+77°. 1H-NMR (400 MHz, MeOH): δ 7.50 (1H, dd, J1 8.4 Hz J2 2.0 Hz), δ 7.41 (1H, d, J 1.6 Hz), δ 7.31 (1H, d, J 7.6 Hz), δ 5.25 (1H, t, J 5.2 Hz), δ 5.03 (2H, dd, J1 50 Hz, J2 16 Hz), δ 3.10 (3H, s), δ 2.97 (2H, m), δ 2.65 (2H, t, J 7.2 Hz), δ 1.56 (2H, m), δ 0.95 (3H, t, J 7.6 Hz).

Provenance & Evidence