反応 #366672

反応方程式

(S)-(−)-1-cyclohexylethylamine

(S)-(−)-limonene oxide

→

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

収率 33.7%

溶媒

water

反応条件

後処理

1. 1
   その他A 100-mL, single-neck flask equipped with a magnetic stirring bar and a reflux condenser
2. 2
   その他fitted with a nitrogen bubbler
3. 3
   温度The mixture was heated
4. 4
   温度to reflux
5. 5
   ろ過filtered
6. 6
   その他to remove an insoluble white solid
7. 7
   workup.DISTILLATIONThe excess limonene oxide was then distilled off at reduced pressure
8. 8
   その他leaving an orange oil
9. 9
   その他that crystallized
10. 10
    workup.WAITupon standing over night
11. 11
    その他The solid was recrystallized from approximately 20 mL of n-heptane

実験手順

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.

出典