反応 #49179

反応方程式

compound 3a

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

Borane THF

→

compound 29

収率 92.1%

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

収率 92.1%

溶媒

THF

反応条件

後処理

1. 1
   その他was brought to room temperature
2. 2
   温度at reflux temperature for over night
3. 3
   温度the reaction mixture was cooled
4. 4
   濃縮concentrated under vacuum to dryness
5. 5
   workup.ADDITIONTo the residue, saturated solution of ammonium chloride (200 mL) was added
6. 6
   抽出the product extracted with ethyl acetate (3×100 mL)
7. 7
   乾燥The combined organic layer was dried over anhydrous sodium sulfate
8. 8
   ろ過filtered
9. 9
   濃縮concentrated under reduced pressure
10. 10
    その他The crude was purified by column chromatography over silica gel

実験手順

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%).

出典