HCID 58677920, compound → HCID 49762843, compound

Participants

Reaction Steps

To a solution of 25.02 g 3-(4-Bromophenyl)-N-methoxy-N-methylpropanamide from Step A above in 500 mL anhydrous ether cooled in an ice bath was added 115 mL 2 M cyclohexylmagnesium bromide in ether over 30 minutes. The cooling bath was removed after finishing addition. After 75 minutes, an additional 30 mL 2 M cyclohexylmagnesium bromide in ether was added. The reaction mixture was stirred for 40 minutes and poured into a mixture containing 500 mL ether, 500 mL cold water, 200 mL saturated brine, and 175 mL 2 N HCl. The layers were separated. The aqueous layer was extracted with 4×75 mL ether. The combined ether solution was washed with 200 mL 1:1 5% NaHCO3 and saturated brine followed by 200 mL saturated brine, dried over anhydrous Na2SO4, and evaporated to give a crude product. It was purified on silica gel using 20-100% EtOAc in hexanes and re-purified using 5-10% EtOAc in hexanes to give the title compound as yellow oil. 1H NMR (CDCl3, 500 MHz) δ 7.39˜7.42 (m, 2H), 7.06˜7.09 (m, 2H), 2.84˜2.87 (m, 2H), 2.74˜2.78 (m, 2H), 2.32 (tt, J=3.3 & 11.3 Hz, 1H), 1.76˜1.84 (m, 4H), 1.65˜1.70 (m, 1H), 1.15˜1.36 (m, 5H).

Provenance & Evidence