Carbon tetrabromide → (6S,7aS)-6-Bromo-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one

참여 물질

반응 단계

Triphenylphosphine (1.7 g, 6.5 mmol) was added to a solution of (6R,7aS)-6-Hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (1.0 g, 3.3 mmol) and CBr4 (2.2 g, 6.6 mmol) in anhydrous THF (50 mL), the mixture was stirred at room temperature for 30 minutes under N2 protection. Then the mixture was filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=3:1) to give 1.15 g (95%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.61 (d, 2H, J=9.3 Hz), 7.21 (d, 2H, J=8.4 Hz), 4.48-4.42 (m, 1H), 4.19 (dd, 1H, J1=13.2 Hz, J2=2.7 Hz), 4.11-4.02 (m, 2H), 3.92-3.88 (m, 1H), 3.53 (dd, 1H, J1=13.5 Hz, J2=5.4 Hz), 2.81-2.71 (m, 1H), 2.26-2.18 (m, 1H). LC-MS: 365.0 [M+1]+.

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