Ethyl Acetate → HCID 86755240, compound

Participants

Reaction Steps

To a solution of trans-1-[4-(4-fluorophenyl)cyclohexyl]-(3R)-pyrrolidin-3-ylamine dihydrochloride (210 mg, 0.63 mmol) in dry tetrahydrofuran (4 mL) was added N,N-diisopropylethylamine (219 μL, 1.26 mmol) followed by (4S,5R)-4-(3,4-difluorophenyl)-2-oxo-5-(tetrahydropyran-2-yloxymethyl)-oxazolidine-3-carboxylic acid 4-nitrophenyl ester (300 mg, 0.63 mmol). The reaction mixture was stirred at ambient temperature for 18 h when the volatiles were removed under reduced pressure and residue dissolved in ethyl acetate (100 mL) and washed with 10% aqueous sodium carbonate solution (8×100 ml), brine (1×100 ml), dried over magnesium sulfate and filtered. The volatiles were removed under reduced pressure and the resulting oil was purified by pressurized silica gel chromatography (3:1 then 1:0 ethyl acetate:hexane to afford (4S,5R)-trans-4-(3,4-difluorophenyl)-5-(tetrahydropyran-2-yloxymethyl-2-oxo-oxazolidine-3-carboxylic acid {1-[4-(4-fluorophenyl)cyclohexyl]-(3R)-pyrrolidin-3-yl}amide as a white foam (153 mg, 0.25 mmol, 40%).

Provenance & Evidence