Triphenylphosphine → (3,5-Bis-trifluoromethyl-benzyl)-[2-(bromo-cyclohexyl-methyl)-5-trifluoromethyl-benzyl]-(2-methyl-2H-tetrazol-5-yl)-amine

Participants

Reaction Steps

To a solution of (2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclohexyl-methanol (51 mg; 0.086 mmol) in methylene chloride (1.2 mL) was added N-bromosuccinimide (63 mg; 0.354 mmol) and triphenylphosphine (97 mg; 0.369 mmol). The reaction was stirred at room temperature for 16 hours. Reaction was directly purified over 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 10-45% ethyl acetate in heptane) to give 27 mg (48% yield) of the title compound as a colorless gum. MS (ES+): Calc: 657.1, Found: 658.3 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 7.78 (s, 1H), 7.71 (d, J=8.30 Hz, 1H), 7.65 (s, 2H), 7.59 (d, J=8.30 Hz, 1H), 7.28 (s, 1H), 4.99 (d, J=9.96 Hz, 1H), 4.91 (d, J=15.35 Hz, 1H), 4.68 (q, J=15.77 Hz, 2H), 4.68 (d, J=16.26 Hz, 1H), 4.24 (s, 3H), 2.34 (d, J=12.86, 1H), 2.00 (m, 1H), 1.80 (d, 13.28 Hz, 1H), 1.63 (t, J=10.35 Hz, 2H), 1.39-1.22 (m, 2H), 1.14 (m, 2H), 0.98 (m, 1H), 0.76 (m, 1H).

Provenance & Evidence