반응 #49179

반응 방정식

compound 3a

[6-(4-Hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-6-oxo-hexyl]-carbamic acid benzyl ester

Borane THF

→

compound 29

수율 92.1%

[6-(4-Hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-hexyl]-carbamic acid benzyl ester

수율 92.1%

용매

THF

반응 조건

후처리

1. 1
   기타was brought to room temperature
2. 2
   온도at reflux temperature for over night
3. 3
   온도the reaction mixture was cooled
4. 4
   농축concentrated under vacuum to dryness
5. 5
   workup.ADDITIONTo the residue, saturated solution of ammonium chloride (200 mL) was added
6. 6
   추출the product extracted with ethyl acetate (3×100 mL)
7. 7
   건조The combined organic layer was dried over anhydrous sodium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated under reduced pressure
10. 10
    기타The crude was purified by column chromatography over silica gel

실험 절차

Referring to scheme 10, compound 3a (7 g, 19.2 mmol) was dissolved in anhydrous THF and cooled to 0° C. under argon atmosphere. Borane-THF (50 mL, 1M soln. in THF, 2.5 equiv.) was added slowly over a period of 15mins. The reaction mixture was brought to room temperature and stirred at reflux temperature for over night. After 16 h, the reaction mixture was cooled and concentrated under vacuum to dryness. To the residue, saturated solution of ammonium chloride (200 mL) was added and the product extracted with ethyl acetate (3×100 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified by column chromatography over silica gel to afford compound 29 as a viscous liquid (6.2 g, 92%).

출처