Triethylamine → (7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]-2-[4-(trifluoromethyl)-benzoyl]hexahydropyrrolo[1,2-a]pyrazin-4(1H)-one

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Reaction Steps

To a solution of the product from Example 174G (100 mg, 0.365 mmol) in dichloromethane (2 mL) were added triethylamine (50.8 μL, 0.365 mmol) followed by 4-(trifluoromethyl)benzoyl chloride (59.7 μL, 0.401 mmol). The mixture was stirred at ambient temperature for 18 hours, and then partitioned between water and dichloromethane. The organic extract was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on a 12 g silica gel column eluting with 5% ethyl acetate/hexanes for 3 minutes and then a gradient to 100% ethyl acetate over 20 minutes to give the title compound (34 mg, 20.9%). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.16 (t, J=8.3 Hz, 2H), 7.83 (d, J=8.2 Hz, 2H), 7.73-7.60 (m, 2H), 5.62-5.41 (m, 1H), 4.85-4.46 (m, 1H), 4.10-3.61 (m, 4H), 3.50-3.34 (m, 1H), 3.24-2.71 (m, 1H), 2.44-1.65 (m, 3H), 1.05-0.90 (m, 2H), 0.87-0.73 (m, 2H); MS (ESI) m/z 447 (M+H)+.

Provenance & Evidence