反应详情

温度

85 °C

Ethyl 3-(dimethylamino)-2-isocyanoacrylate (300 mg) and trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexylamine (Synthetic Communications, 1990, Vol. 20, p. 1073) (1.02 g) were mixed and stirred at 85° C. for 12 hours. To the reaction solution, saturated aqueous ammonium chloride was added, and organic matter was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate-4/1-1/1). Lithium aluminum hydride (92%, 105 mg) was suspended in tetrahydrofuran (8 mL). The produced crude product was dissolved in tetrahydrofuran (6 mL), and this solution was slowly added dropwise to the suspension at 0° C. After stirring at 0° C. for 1 hour, the reaction solution was diluted with diethyl ether, and saturated aqueous sodium sulfate was added thereto. After stirring at room temperature for 1 hour, the formed inorganic salt was removed by filtration through celite. The filtrate was concentrated under reduced pressure to obtain a crude product. This crude product was washed with a mixed solvent of hexane and ethyl acetate (2:1) to obtain the title compound (260 mg).

1. extractionorganic matter was extracted with ethyl acetate
2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
3. filtrationfiltered
4. distillationthe solvent was distilled off under reduced pressure
5. customThe residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate-4/1-1/1)
6. customThe produced crude product
7. additionthis solution was slowly added dropwise to the suspension at 0° C
8. stirringAfter stirring at 0° C. for 1 hour
9. additionwas added
10. stirringAfter stirring at room temperature for 1 hour
11. customthe formed inorganic salt was removed by filtration through celite
12. concentrationThe filtrate was concentrated under reduced pressure
13. customto obtain a crude product
14. washThis crude product was washed with a mixed solvent of hexane and ethyl acetate (2:1)