Sodium Iodide → 1-(Diphenylmethyl)-3-{[(2-fluorophenyl)sulfonyl]methyl}azetidine

Participants

Reaction Steps

[1-(Diphenylmethyl)azetidin-3-yl]methyl methanesulfonate [Example 1, step 1] (3.15 g, 9.50 mmol), sodium 2-fluorobenzenesulfinate (2.65 g, 14.3 mmol) and sodium iodide (2.18 g, 14.5 mmol) were reacted in dimethylformamide (50 mL) by the procedure of Example I Step 3a to afford the title compound (1.37 g, 36%); 1H NMR (500 MHz, CDCl3) δ 2.80–2.88 (3H, m), 3.33 (2H, t, J=7.0 Hz), 3.57 (2H, d, J=6.9 Hz), 4.28 (1H, s), 7.16 (2H, t, J=7.3 Hz), 7.20–7.26 (5H, m), 7.29–7.35 (5H, m), 7.61–7.65 (1H, m), 7.86–7.90 (1H, m); 19F NMR (471 MHz, CDCl3) δ −108.9; m/z (ES+) 396 ([M+H]+, 100%).

Provenance & Evidence