Ethyl Acetate → HCID 58968712, compound

Participants

Reaction Steps

To a solution of 1,-(2-(((3,5-bis(trifluoromethyl)benzyl)(2-methyl-2-H-tetrazol-5-yl)amino)methyl)-4-(trifluoromethyl)phenyl-2-cyclopentylethanone (160 mg, 0.269 mmol) in anhydrous THF (10 mL) at 0° C. was added methylmagnesium bromide (3.0 M solution in THF, 0.359 mL, 1.07 mmol). After stirring for 30 minutes the solution was warmed to room temp and stirred for 1.5 hours. After 1.5 hours solution was portioned between 2 N HCL (10 mL) and ethyl acetate (20 mL). The mixture was stirred at room temperature for 10 minutes before the layers were separated. The aqueous layer was extracted with ethyl acetate (3×15 mL). The combined organics layers were dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give a yellow oil. (160 mg, 97%). 1H NMR (400 MHz, CDCl3) δ 7.72 (s, 1H) 7.67(s, 2H) 7.38 (m, 3H) 5.32 (d, J=16.6 Hz, 1H) 5.01 (d, J=16.6 Hz, 1H) 4.78 (s, 2H) 4.13 (s, 3H) 1.92 (dd, J=5.4 Hz, J=5.4 Hz) 1.80 (dd, J=5.81 Hz, J=6.24 Hz) 1.64 (m, 2H) 1.59 (s, 3H) 1.54 (m, 3H) 1.35 (m, 2H) 0.88 (m, 2H). LC-MS Calc. 609.5, found 610.5 (M+H).

Provenance & Evidence