Triacetoxyperiodinane → (2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclohexyl-methanone

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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 (5.46 g, 9.17 mmol) in methylene chloride (150 mL) at room temperature was added Dess-Martin periodinane (4.36 g, 10.3 mmol). The mixture was stirred at room temperature for 2 hours, diluted with ether (50 mL) and 1N sodium hydroxide (40 mL) was added. The mixture was extracted with ethyl acetate (2×100 mL). Combined organic layers were washed with 1N sodium hydroxide (2×40 mL), brine (50 mL), dried with sodium sulfate and concentrated in vacuo. The crude was purified by chromatography over 40+M Biotage silica column (eluted with 0-30% ethyl acetate in heptane) to afford the title compound as a pale yellow oil (5.2 g, 96%). 1H NMR (400 MHz, CDCl3) δ ppm 1.16-1.42 (m, 5H) 1.70 (d, J=12.03 Hz, 1H) 1.80 (d, J=9.54 Hz, 4H) 2.96-3.05 (m, 1H) 4.18 (s, 3H) 4.79 (s, 2H) 4.82 (s, 2H) 7.53 (s, 1H) 7.57 (d, J=8.30 Hz, 1H) 7.64 (d, J=7.88 Hz, 1H) 7.66 (s, 2H) 7.72 (s, 1H). MS (ES+) Calc: 593.2, Found: 594.5 (M+1)

Provenance & Evidence