Carbon tetrabromide → HCID 86673575, compound

Participants

Reaction Steps

To the solution of (6S,7aS)-6-Hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (example 20, step a) (1.47 g, 4.36 mmol) and CBr4 (3.3 g, 8.72 mmol) in anhydrous THF (30 mL) was added PPh3 (2.3 g, 8.72 mmol) in THF (10 mL). Then the mixture was filtered and concentrated. The residue was purified by silica gel column chromatography (eluting with petroleum ether/ethyl acetate=10:1) to yield 1.50 g (84%) of the title compound as white solid. 1H NMR (300 MHz, CDCl3): δ 7.58 (d, 2H, J=9 Hz), 7.17 (d, 2H, J=9 Hz), 4.59-4.55 (m, 1H), 4.43-4.37 (m, 1H), 4.25-4.22 (m, 1H), 4.07 (t, 1H, J=9 Hz), 3.76 (dd, 1H, J1=3 Hz, J2=9 Hz), 3.62-3.56 (d, 1H, J=18 Hz), 2.43 (dd, 1H, J1=6 Hz J2=12 Hz), 1.99-1.92 (m, 1H). LC-MS: 365 [M+1]+.

Provenance & Evidence