4-Methylmorpholine → (R)-4-methyl-3-{4-[4-(4-methylbenzoyl)piperidine-1-carbonyl]phenyl}oxazolidin-2-one

Participants

Reaction Steps

To a mixture of (R)-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acid (633 mg) described in Preparation Example 37, (4-methylphenyl)piperidin-4-ylmethanone hydrochloride (719 mg) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (1.2 g) were added chloroform (3 mL), methanol (3 mL) and N-methylmorpholine (330 μL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 1N aqueous sodium hydroxide solution, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (989 mg).

Provenance & Evidence