Reacción #366672

Ecuación de reacción

(S)-(−)-1-cyclohexylethylamine

(S)-(−)-limonene oxide

→

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

Rendimiento 33.7%

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
   Filtraciónfiltered
6. 6
   Otroto remove an insoluble white solid
7. 7
   workup.DISTILLATIONThe excess limonene oxide was then distilled off at reduced pressure
8. 8
   Otroleaving an orange oil
9. 9
   Otrothat crystallized
10. 10
    workup.WAITupon standing over night
11. 11
    OtroThe solid was recrystallized from approximately 20 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 4.75 g (0.037 mol) of (S)-(−)-1-cyclohexylethylamine, 23.00 g (0.151 mol) of (S)-(−)-limonene oxide, and 2.0 mL of deionized water. The mixture was heated to reflux and held there for 109.75 h. The reaction mixture was cooled to room temperature and filtered to remove an insoluble white solid. The excess limonene oxide was then distilled off at reduced pressure leaving an orange oil that crystallized upon standing over night. The solid was recrystallized from approximately 20 mL of n-heptane to give 3.48 g of (1R,2R,4S)-2-((1S)-1-cyclohexylethylamino)-1-methyl-4-(1-methylethenyl) cyclohexanol, as a white solid, mp 63-64° C.

Fuente