Cyclohexane → HCID 57546173, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-1-(5-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indol-7-yl)ethyl 2,2,2-trichloroacetimidate (361 mg, 0.716 mmol) and tert-butyl 4-(4-fluorophenyl)-4-(hydroxymethyl)piperidine-1-carboxylate (244 mg, 0.788 mmol) at 0° C. was added cyclohexane (2 ml, 18.49 mmol) and fluoroboric acid diethyl ether complex (0.019 ml, 0.143 mmol). The reaction was stirred at 0° C. for 45 min and was judged complete by TLC. The reaction was quenched with aqueous sodium bicarbonate (5 mL) and extracted with ethyl acetate (3×5 mL). The combined organic layers were dried with magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel with a gradient of ethyl acetate/hexanes from 12% to 100%. The product (245 mg, 0.376 mmol, 52.5% yield) was isolated as a clear oil. 1H-NMR (CDCl3, 400 MHz) δ 7.77 (m, 1H), 7.34 (s, 1H), 7.18 (m, 2H), 7.08 (d, J=3.7 Hz, 1H), 6.94 (m, 2H), 6.54 (m, 1H), 5.29 (m, 2H), 5.18 (m, 1H), 3.65 (m, 2H), 3.33 (m, 2H), 3.24 (m, 1H), 3.14 (m, 1H), 3.00 (m, 2H), 2.03 (m, 2H), 1.86 (m, 2H), 1.44 (d, J=6.4 Hz, 3H), 1.419 (s, 9H), 0.74 (m, 2H), −0.09 (s, 9H); LC/MS (HPLC method 4): tR=4.871 min, 651.28(MH)+.

Provenance & Evidence