تفاعل #366672

معادلة التفاعل

(S)-(−)-1-cyclohexylethylamine

(S)-(−)-limonene oxide

→

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

المردود 33.7%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   أخرىA 100-mL, single-neck flask equipped with a magnetic stirring bar and a reflux condenser
2. 2
   أخرىfitted with a nitrogen bubbler
3. 3
   درجة الحرارةThe mixture was heated
4. 4
   درجة الحرارةto reflux
5. 5
   ترشيحfiltered
6. 6
   أخرىto remove an insoluble white solid
7. 7
   workup.DISTILLATIONThe excess limonene oxide was then distilled off at reduced pressure
8. 8
   أخرىleaving an orange oil
9. 9
   أخرىthat crystallized
10. 10
    workup.WAITupon standing over night
11. 11
    أخرىThe solid was recrystallized from approximately 20 mL of n-heptane

الإجراء التجريبي

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.

المصدر