Water → (6R,7aS)-6-(1-Phenyl-ethoxy)-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one

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Reaction Steps

NaH (70% in oil, 7 mg, 0.2 mmol) was added to a solution of (6R,7aS)-6-Hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (example 1, step e) (50 mg, 0.165 mmol) and (1-Bromo-ethyl)-benzene (40 mg, 0.21 mmol) in anhydrous THF (10 mL), the mixture was refluxed overnight. The mixture was cooled and poured into water (20 mL), extracted with ethyl acetate (3×20 mL), the organic layers was combined, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=7:1) to give 20 mg (30%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.57 (dd, 2H, J1=9.0 Hz, J2=1.8 Hz), 7.38-7.26 (m, 5H), 7.17 (d, 2H, J=9.0 Hz), 4.52-4.42 (m, 1H), 4.12-3.84 (m, 4H), 3.71-3.61 (m, 1H), 3.27-3.06 (m, 1H), 2.28-2.02 (m, 1H), 1.49-1.37 (m, 4H); LC-MS: 407.0 [M+1]+.

Provenance & Evidence