Chlorotrimethylsilane → HCID 24953999, compound

Participants

Reaction Steps

3-(2-(4-(Dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)propyl acetate (less polar diastereomer) (190 mg, 0.51 mmol) was dissolved in ethyl acetate (50 ml). Me3SiCl (128 μl, 1.02 mmol) was then added dropwise at RT. The mixture was stirred for 1 h. A white precipitate precipitated out. The precipitate was filtered off with suction, washed with ethyl acetate (2×5 ml) and then dried. Example 186 (120 mg, m.p. 217-220° C., 58%) was a white solid 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.68-2.03-(m, 10H), 2.37-2.47 (m, 1H), 2.54-2.62 (m, 6H), 2.68-2.78 (m, 2H), 2.98-3.11 (m, 1H), 3.12-3.22 (m, 2H), 3.93 (t, J=6.50, 6.50 Hz, 2H), 6.87-7.06 (m, 2H), 7.25 (d, J=7.80 Hz, 1H), 7.42 (d, J=7.80, 1 H) 7.48-7.60 (m, 3H), 7.67-7.82-(m, 2H), 10.00 (s, 1H), 11.34 (s, 1H)

Provenance & Evidence