Reaktion #366672

Reaktionsgleichung

(S)-(−)-1-cyclohexylethylamine

(S)-(−)-limonene oxide

→

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

Ausbeute 33.7%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 100-mL, single-neck flask equipped with a magnetic stirring bar and a reflux condenser
2. 2
   Sonstigefitted with a nitrogen bubbler
3. 3
   TemperaturThe mixture was heated
4. 4
   Temperaturto reflux
5. 5
   Filtrationfiltered
6. 6
   Sonstigeto remove an insoluble white solid
7. 7
   workup.DISTILLATIONThe excess limonene oxide was then distilled off at reduced pressure
8. 8
   Sonstigeleaving an orange oil
9. 9
   Sonstigethat crystallized
10. 10
    workup.WAITupon standing over night
11. 11
    SonstigeThe solid was recrystallized from approximately 20 mL of n-heptane

Vorschrift

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.

Quelle