4-Methylbenzenethiol → (6R,7aS)-6-p-Tolylsulfanyl-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one

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Reaction Steps

Na (112 mg, 0.548 mmol) was added to anhydrous enthanol (10 ml). Until the sodium was dissolved. 4-methylbenzenethiol (34 mg, 0.0274 mmol) was added in the ice-bath. Subsequently (6S,7aS)-6-Bromo-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (100 mg, 0.274 mmol) was added. After the addition, the ice bath was removed and the reaction was stirred for overnight at the room temperature. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to yield 100 mg (85%) of the title compounds as white solid. 1H NMR (300 MHz, CDCl3): δ 7.61-7.56 (m, 2H), 7.33-7.29 (m, 2H), 7.20-7.12 (m, 4H), 4.28-4.00 (m, 3H), 3.85-3.83 (m, 1H), 3.69 (dd, 1H, J1=2.7 Hz, J2=9.6 Hz), 3.11 (dd, 1H, J1=4.2 Hz, J2=12.9 Hz), 2.32 (s, 3H), 2.19-2.12 (m, 1H), 1.93-1.83 (m, 1H); LC-MS: 409 [M+1]+.

Provenance & Evidence