HCID 54674497, compound → HCID 54674652, compound

Participants

Reaction Conditions

Reaction Steps

Phenylmagnesium bromide in tetrahydrofuran (0.266 mL, 0.266 mmol) was added to (3aR,6aS)-2-[6-(trifluoromethyl)pyridin-2-yl]hexahydrocyclopenta[c]pyrrol-4(1H)-one (60 mg, 0.222 mmol) from Example 32 in tetrahydrofuran (1 mL) at −40° C., and the reaction mixture was allowed to warm to −10° C. in 20 minutes. The reaction was quenched with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The combined organic washes were purified by silica gel chromatography using 0-40% ethyl acetate/hexane as eluent to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.78 (dt, J=8.2, 1.6, 2H), 7.45 (t, J=7.7, 3H), 7.37-7.27 (m, 1H), 6.90 (d, J=7.2, 1H), 6.70 (d, J=0.5, 1H), 6.46 (d, J=8.6, 1H), 4.02-3.94 (m, 1H), 3.92-3.82 (m, 1H), 3.62-3.42 (m, 2H), 3.07 (td, J=9.3, 2.8, 1H), 3.02-2.92 (m, 1H), 2.38-2.22 (m, 2H), 2.17-1.98 (m, 2H); MS (ESI+) m/z 349 (M+H)+.

Provenance & Evidence