反应详情

To a solution of (E)-1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxylic acid (1.0 g, 3.04 mmol) in ethyl acetate (10.6 mL) under a nitrogen atmosphere at room temperature was added dimethylformamide (1 drop), pyridine (0.49 mL, 6.08 mmol) and thionyl chloride (0.28 mL, 3.95 mmol) and the mixture stirred at room temperature for 40 minutes. Benzyl cis-4-amino-1-cyclohexanecarboxylate p-toluenesulphonate (1.29 g, 3.19 mmol) was added at room temperature followed by triethylamine (1.27 mL, 9.12 mmol) and the mixture stirred at room temperature for 3 hours. The reaction mixture was diluted with distilled water (50 mL) and ethyl acetate (50 mL) and the layers separated. The ethyl acetate layer was washed with distilled water (2×50 mL), 1.0M aqueous hydrochloric acid solution (50 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give a brown oil (1.552 g). The crude product was purified by chromatography on silica by elution with hexane/ethyl acetate (1:1) to give, after combination and evaporation of appropriate fractions, the title compound as an oil (1.07 g, 65%).

1. stirringthe mixture stirred at room temperature for 3 hours
2. customthe layers separated
3. washThe ethyl acetate layer was washed with distilled water (2×50 mL), 1.0M aqueous hydrochloric acid solution (50 mL)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure