Reaktion #366673

Reaktionsgleichung

1-adamantylamine

(S)-(−)-limonene oxide

→

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

Ausbeute 39.8%

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
   FiltrationThe reaction mixture was filtered
6. 6
   Sonstigeto remove some insoluble material
7. 7
   WaschenThe filter paper was washed with a small amount of n-heptane
8. 8
   TemperaturUpon cooling
9. 9
   SonstigeThe solid was isolated by filtration
10. 10
    Waschenwashed with a small amount of n-heptane, air
11. 11
    Sonstigedried
12. 12
    Sonstigevacuum dried at 40° C
13. 13
    TemperaturThe filtrate was cooled in a freezer
14. 14
    Sonstigeto give a second crop of crystals that
15. 15
    Sonstigewere isolated
16. 16
    Sonstigedried in the same manner
17. 17
    Sonstigerecrystallized from 75 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 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.

Quelle