反应详情

温度

110 °C

2-Adamantanamine hydrochloride (1.641 g, 8.74 mmol) was added to 5-(cyclopentanecarbonyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (Intermediate#77), (2.1 g, 8.74 mmol) and N-Ethyldiisopropylamine (1.512 mL, 8.74 mmol) in toluene (30 mL). The resulting suspension was stirred at 110° C. for 2 hours. The reaction mixture was diluted with EtOAc (100 mL), and washed sequentially with 2M HCl (20 mL), and water (2×50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford N-(2-adamantyl)-3-cyclopentyl-3-oxo-propanamide (1.030 g, 40.7%) as a brown oil which crystallised on standing.

1. washwashed sequentially with 2M HCl (20 mL), and water (2×50 mL)
2. dry with materialThe organic layer was dried over MgSO4
3. filtrationfiltered
4. customevaporated
5. customto afford crude product
6. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane
7. customPure fractions were evaporated to dryness