Methyl iodide → 4-[3',5'-Dichloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-carbonyl]-1-methyl-piperazin-2-one

Participants

Reaction Steps

Treat a solution of racemic 1-cyclohexyl-3-[3,5-dichloro-4′-(hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-biphenyl-4-ylmethyl]-pyrrolidin-2-on (0.245 g, 0.46 mmol) in dimethylformamide (6 mL) with 60% sodium hydride (0.037 g, 0.93 mmol) and stir for 15 minutes at room temperature under a nitrogen atmosphere. Cool the reaction to 0° C., treat with iodomethane (0.25 g, 1.76 mmol) and then stir at room temperature for 16 hours under a nitrogen atmosphere. Quench the reaction with 1N hydrochloric acid, dilute with ethyl acetate and wash with water. Dry the organic layer with sodium sulfate and purify by silica gel chromatography using a gradient of 0 to 10% methanol in dichloromethane to afford product. Re-crystallize from acetone/diethyl ether to afford 81 mg (32%) of the title compound: MS (m/z) 542 (M+).

Provenance & Evidence