Water → Propyl-carbamic acid (6R,7aS)-3-oxo-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-6-yl ester

Beteiligte Stoffe

Reaktionsschritte

1-Isocyanatopropane (30 mg, 0.4 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) (60 mg, 0.2 mmol) in anhydrous THF (10 mL) and pyridine (2 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 (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=4:1) to give final compound 20 mg (26%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.60 (d, 2H, J=9.0 Hz), 7.19 (d, 2H, J=8.7 Hz), 5.35 (t, 1H, J=5.7), 4.71 (s, 1H), 4.17-4.00 (m, 3H), 3.74 (d, 1H, J=7.2 Hz), 3.22-3.12 (m, 3H), 2.23 (dd, 1H, J1=12.9 Hz, J2=3.3 Hz), 1.71-1.48 (m, 3H), 0.94 (t, 3H, J=7.2 Hz); LC-MS: 388.1 [M+1]+.

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