반응 #454527

반응 방정식

(-)-(2R)-2-[4-Benzyloxy-3-(2-benzyloxyethyl)phenyl]-2-hydroxy-N-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide

triethanolamine

water

→

(-)-(1R)-1-[4-benzyloxy-3-(2-benzyloxyethyl)phenyl]-2-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-ylamino)ethanol

수율 65.3%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITION438 μl of borane-dimethylsulfide complex was added to the solution
2. 2
   온도the mixture was heated
3. 3
   온도under reflux for 3 hours
4. 4
   온도the mixture was again heated
5. 5
   온도under reflux for 6 hours
6. 6
   온도After cooling
7. 7
   추출the mixture was extracted with ethyl acetate
8. 8
   세척The extract was washed with water
9. 9
   건조dried over anhydrous magnesium sulfate
10. 10
    기타Thereafter, the solvent was evaporated under reduced pressure
11. 11
    기타the resulting residue was recrystallized from ethyl acetate

실험 절차

(-)-(2R)-2-[4-Benzyloxy-3-(2-benzyloxyethyl)phenyl]-2-hydroxy-N-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (low polarity isomer) (1.08 g) was dissolved in 20 ml of tetrahydrofuran, 438 μl of borane-dimethylsulfide complex was added to the solution, and the mixture was heated under reflux for 3 hours. Then, a solution of 1.14 g of triethanolamine in 1 ml of tetrahydrofuran was added and the mixture was again heated under reflux for 6 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. Thereafter, the solvent was evaporated under reduced pressure and the resulting residue was recrystallized from ethyl acetate to give 687 mg of (-)-(1R)-1-[4-benzyloxy-3-(2-benzyloxyethyl)phenyl]-2-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-ylamino)ethanol having a melting point of 147 to 150° C.

출처