反应详情

A 100-mL, single-neck flask equipped with a magnetic stirring bar and a reflux condenser fitted with a nitrogen bubbler was charged with 7.71 g (0.051 mol) of 1-adamantylamine, 22.83 g (0.150 mol) of (S)-(−)-limonene oxide, and 4.0 mL of deionized water. The mixture was heated to reflux and held there for 31 days. The reaction mixture was filtered to remove some insoluble material. The filter paper was washed with a small amount of n-heptane. Upon cooling, the filtrate solidified to a nearly completely solid mass. The solid was isolated by filtration, washed with a small amount of n-heptane, air dried, and vacuum dried at 40° C. The filtrate was cooled in a freezer to give a second crop of crystals that were isolated and dried in the same manner. The two crops of crystals were combined and recrystallized from 75 mL of n-heptane to give 6.16 g of (1R,2R,4S)-2-(1-adamantylamino)-1-methyl-4-(1-methylethenyl)cyclohexanol as a white solid, mp 94-96° C.

1. customA 100-mL, single-neck flask equipped with a magnetic stirring bar and a reflux condenser
2. customfitted with a nitrogen bubbler
3. temperatureThe mixture was heated
4. temperatureto reflux
5. filtrationThe reaction mixture was filtered
6. customto remove some insoluble material
7. washThe filter paper was washed with a small amount of n-heptane
8. temperatureUpon cooling
9. customThe solid was isolated by filtration
10. washwashed with a small amount of n-heptane, air
11. customdried
12. customvacuum dried at 40° C
13. temperatureThe filtrate was cooled in a freezer
14. customto give a second crop of crystals that
15. customwere isolated
16. customdried in the same manner
17. customrecrystallized from 75 mL of n-heptane