Methanesulfonyl chloride → 4-(Chloromethyl)-5-cyclopropyl-3-((trans)-2-(trifluoromethyl)cyclohexyl)isoxazole

Participants

Reaction Steps

A cold (0°C.) solution of (5-cyclopropyl-3-((1S,2S)-2-(trifluoromethyl)cyclohexyl) isoxazol-4-yl)methanol (1.8 g, 6.2 mmol) dichloromethane was treated with Hunig's base (953 μL, 6.8 mmol) followed by methane sulfonyl chloride (508 L, 6.5 mmol). Afte(6 hr of stirring, the reaction was treated with H2O and phases separated. The organic phase was collected, dried (MgSO4), filtered, concentrated, and chromatographed (SiO2, linear gradient, 0-80% EtOAc in Hex) to give the title compound. 1H NMR (400 MHz, CDCl3) δ 4.48 (dd, J=36.5, 12.6 Hz, 2H), 3.48 (m, 1H), 2.44 (m, 1H), 2.15 (ddd, J=25.5, 12.8, 3.6 Hz, 1H), 2.04-1.87 (m, 4H), 1.82-1.68 (m, 2H), 1.55 (m, 1H), 1.35 (m, 1H), 1.14 (m, 2H), 1.09 (m, 2H), MS m/z 308.1 (M+1).

Provenance & Evidence