Water → HCID 70976107, Verbindung

Beteiligte Stoffe

Reaktionsschritte

NaH (25 mg, 70% in oil, 0.7 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) (300 mg, 1 mmol) in anhydrous THF (10 mL), the mixture was stirred at room temperature for 0.5 hour, then 2-propyloxirane (300 mg, 3.5 mmol) was added to the solution, the mixture was stirred at 75° C. overnight in a sealed tube. The mixture was cooled and poured into water (50 mL), extracted with ethyl acetate (3×30 mL), the organic layers was combined and washed with brine, dried over anhydrous sodium sulphate, filtered and concentrated. The residue was purified by silica gel column chromatography (eluting with petroleum ether/ethyl acetate=4:1) to yield 100 mg (26%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.62 (d, 2H, J=8.7 Hz), 7.19 (d, 2H, J=8.7 Hz), 4.20 (t, 1H, J=5.7 Hz), 4.09-4.00 (m, 3H), 3.82-3.74 (m, 2H), 3.52-3.43 (m, 1H), 3.37-3.18 (m, 2H), 2.26-2.10 (m, 2H), 1.60-1.38 (m, 5H), 0.96 (t, 3H, J=6.9 Hz); LC-MS: 389.1 [M+1]+.

Herkunft & Nachweise