HCID 54674497, compound → HCID 54674650, compound

Participants

Reaction Steps

Methylmagnesium iodide in ether (0.302 mL, 0.907 mmol) was added to (3aR,6aS)-2-[6-(trifluoromethyl)pyridin-2-yl]hexahydrocyclopenta[c]pyrrol-4(1H)-one (70 mg, 0.259 mmol) from Example 32 in ether (0.1 mL) at 25° C., and the reaction mixture was stirred for 1 hour. 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 0-30% ethyl acetate/hexane as eluent to give the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.46 (t, J=7.9, 1H), 6.93 (d, J=7.2, 1H), 6.50 (d, J=8.6, 1H), 5.92 (s, 1H), 4.03 (dd, J=11.1, 3.7, 1H), 3.69 (t, J=9.4, 1H), 3.61-3.50 (m, 1H), 3.43 (dd, J=10.0, 5.7, 1H), 2.83-2.69 (m, 1H), 2.46 (td, J=9.0, 3.9, 1H), 2.14-2.02 (m, 1H), 1.90 (dq, J=11.6, 8.4, 1H), 1.79-1.62 (m, 2H), 1.42 (s, 3H); MS (ESI+) m/z 287 (M+H)+.

Provenance & Evidence