反応 #366673

反応方程式

1-adamantylamine

(S)-(−)-limonene oxide

→

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

収率 39.8%

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The reaction mixture was filtered
6. 6
   その他to remove some insoluble material
7. 7
   洗浄The filter paper was washed with a small amount of n-heptane
8. 8
   温度Upon cooling
9. 9
   その他The solid was isolated by filtration
10. 10
    洗浄washed with a small amount of n-heptane, air
11. 11
    その他dried
12. 12
    その他vacuum dried at 40° C
13. 13
    温度The filtrate was cooled in a freezer
14. 14
    その他to give a second crop of crystals that
15. 15
    その他were isolated
16. 16
    その他dried in the same manner
17. 17
    その他recrystallized from 75 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 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.

出典