Reacción #366673

Ecuación de reacción

1-adamantylamine

(S)-(−)-limonene oxide

→

(1R,2R,4S)-2-(1-adamantylamino)-1-methyl-4-(1-methylethenyl)cyclohexanol

Rendimiento 39.8%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA 100-mL, single-neck flask equipped with a magnetic stirring bar and a reflux condenser
2. 2
   Otrofitted with a nitrogen bubbler
3. 3
   TemperaturaThe mixture was heated
4. 4
   Temperaturato reflux
5. 5
   FiltraciónThe reaction mixture was filtered
6. 6
   Otroto remove some insoluble material
7. 7
   LavadoThe filter paper was washed with a small amount of n-heptane
8. 8
   TemperaturaUpon cooling
9. 9
   OtroThe solid was isolated by filtration
10. 10
    Lavadowashed with a small amount of n-heptane, air
11. 11
    Otrodried
12. 12
    Otrovacuum dried at 40° C
13. 13
    TemperaturaThe filtrate was cooled in a freezer
14. 14
    Otroto give a second crop of crystals that
15. 15
    Otrowere isolated
16. 16
    Otrodried in the same manner
17. 17
    Otrorecrystallized from 75 mL of n-heptane

Procedimiento

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.

Fuente