反应详情

A mixture of 2.4 g. (6.06 mm.) of 5,5-dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine, 1.35 g. (6.06 mm.) of δ-piperidinovaleric acid hydrochloride and 1.30 g. (6.30 mm.) of dicyclohexylcarbodiimide in 100 ml. of methylene chloride was stirred at room temperature for 5 hours. The reaction mixture was cooled overnight in the refrigerator and the by-product of dicyclohexylurea removed by suction filtration. The mother liquor was evaporated to give a golden, viscous residue which was dissolved in a mixture of methylene chloride/cyclohexane and allowed to stand in the cold for 2 hours. Gravity filtration separated a small amount of solid which had appeared, and the solvents were removed using a rotary evaporator. Crystallization from methylene chloride/diethyl ether gave 2.5 g. (69%) of colorless crystals, m.p. 140°-144° C., The sample was pure by thin layer chromatography (10% MeOH/CHCl3) and the infrared and nuclear magnetic resonance spectra were in agreement with the proposed structure.

1. additionA mixture of 2.4 g
2. temperatureThe reaction mixture was cooled overnight in the refrigerator
3. customthe by-product of dicyclohexylurea removed by suction filtration
4. customThe mother liquor was evaporated
5. customto give a golden, viscous residue which
6. customcold for 2 hours
7. filtrationGravity filtration
8. customseparated a small amount of solid which
9. customthe solvents were removed
10. customa rotary evaporator
11. customCrystallization from methylene chloride/diethyl ether
12. customgave 2.5 g