Dimethyl Sulfone → HCID 54161446, compound

Participants

Reaction Steps

1-(3-Cyclopentyloxy-4-methoxyphenyl)-2-methylsulfonylethylamine was prepared by the procedure of Example 1 from dimethyl sulfone (23.14 g, 246.1 mmol) and n-butyllithium (100 mL, 2.5 M, 250 mmol) in tetrahydrofuran (700 mL), and 3-cyclopentyloxy-4-methoxybenzaldehyde (49.50 g, 224.7 mmol), lithium hexamethyldisilazide (246 mL, 1.0 M, 246 mmol) and boron trifluoride etherate (58 mL, 458 mmol) in tetrahydrofuran (200 mL). The product was obtained as a white solid (26.53 g, 38% yield): mp, 155.0-158.0° C.; 1H NMR (CDCl3); δ 1.60-1.65 & 1.81-1.96 (m, 8H, C5H8), 2.91 (s, 3H, CH3), 3.22 (dd, J=3.7, 14.2 Hz, 1H, CHH), 3.33 (dd, J=9.1, 14.1 Hz, 1H, CHH), 3.84 (s, 3H, CH3), 4.58 (q, J=3.7, 9.0 Hz, 1H, NCH), 4.77-4.82 (m, 1H, OCH), 6.82-6.92 (m, 3H, Ar); 13C NMR (CDCl3) δ 23.95, 32.76, 42.42, 50.96, 56.11, 63.22, 80.56, 112.21, 113.00, 118.18, 135.53, 148.09, 149.89; Anal Calcd for C15H23NO4S: C, 57.49; H, 7.40; N, 4.47. Found: C, 58.14; H, 7.42; N, 4.37.

Provenance & Evidence