反应详情

To a solution of rac-[(3R,4S)-4-(3,4-dichloro-phenyl)-1-(piperidine-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester (100 mg, 0.20 mmol) in N-methylpyrrolidinone (1 mL) was added 2-bromo-1,3,4-thiadiazole (50 mg, 0.30 mmol) and N,N-diisopropyl ethyl amine (69 μl, 0.40 mmol). The solution was irradiated in the microwave for 35 min at 150° C. The reaction mixture was diluted with ethyl acetate (15 mL) and washed with an aqueous solution of sodium carbonate (1 M, 15 mL). The organic layer was separated and washed with brine (15 mL) and the aqueous layers were extracted with ethyl acetate (20 mL). The combined organic layers were dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, ethyl acetate:methanol=100:0 to 80:20) afforded the title compound (37 mg, 32%) as an off-white foam. MS m/e: 578.1 [M]+.

1. customThe solution was irradiated in the microwave for 35 min at 150° C
2. washwashed with an aqueous solution of sodium carbonate (1 M, 15 mL)
3. customThe organic layer was separated
4. washwashed with brine (15 mL)
5. extractionthe aqueous layers were extracted with ethyl acetate (20 mL)
6. dry with materialThe combined organic layers were dried over sodium sulfate
7. concentrationconcentrated
8. customPurification by chromatography (SiO2, ethyl acetate:methanol=100:0 to 80:20)