تفاعل #366673

معادلة التفاعل

1-adamantylamine

(S)-(−)-limonene oxide

→

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

المردود 39.8%

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
   ترشيحThe reaction mixture was filtered
6. 6
   أخرىto remove some insoluble material
7. 7
   غسيلThe filter paper was washed with a small amount of n-heptane
8. 8
   درجة الحرارةUpon cooling
9. 9
   أخرىThe solid was isolated by filtration
10. 10
    غسيلwashed with a small amount of n-heptane, air
11. 11
    أخرىdried
12. 12
    أخرىvacuum dried at 40° C
13. 13
    درجة الحرارةThe filtrate was cooled in a freezer
14. 14
    أخرىto give a second crop of crystals that
15. 15
    أخرىwere isolated
16. 16
    أخرىdried in the same manner
17. 17
    أخرىrecrystallized from 75 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 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.

المصدر