반응 #454516

반응 방정식

(-)-(2R)-2-(2,2-Dimethylbenzo[1,2-d]-1,3-dioxan-6-yl)-2-hydroxy-N-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide

triethanolamine

water

→

(-)-(1R)-1-(2,2-dimethylbenzo[1,2-d]-1,3-dioxan-6-yl)-2-[((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]ethanol

수율 84.7%

용매

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도under reflux for 3 hours
3. 3
   온도the mixture was again heated
4. 4
   온도under reflux for 15 hours
5. 5
   온도After cooling
6. 6
   추출the mixture was extracted with ethyl acetate
7. 7
   세척The extract was washed with water
8. 8
   건조dried over anhydrous magnesium sulfate
9. 9
   기타The solvent was evaporated under reduced pressure
10. 10
    기타the resulting residue was recrystallized from ethyl acetate

실험 절차

(-)-(2R)-2-(2,2-Dimethylbenzo[1,2-d]-1,3-dioxan-6-yl)-2-hydroxy-N-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (686 mg) was dissolved in 50 ml of tetrahydrofuran, 3.58 ml of 2 M borane-dimethylsulfide complex in tetrahydrofuran was added, and the mixture was heated under reflux for 3 hours. Then, a solution of 1.34 g of triethanolamine in 5.0 ml of tetrahydrofuran was added, and the mixture was again heated under reflux for 15 hours. After cooling, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was recrystallized from ethyl acetate to give 560 mg of (-)-(1R)-1-(2,2-dimethylbenzo[1,2-d]-1,3-dioxan-6-yl)-2-[((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]ethanol having a melting point of 156 to 158° C.

출처