تفاعل #49179

معادلة التفاعل

compound 3a

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

Borane THF

→

compound 29

المردود 92.1%

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

المردود 92.1%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىwas brought to room temperature
2. 2
   درجة الحرارةat reflux temperature for over night
3. 3
   درجة الحرارةthe reaction mixture was cooled
4. 4
   تركيزconcentrated under vacuum to dryness
5. 5
   workup.ADDITIONTo the residue, saturated solution of ammonium chloride (200 mL) was added
6. 6
   استخلاصthe product extracted with ethyl acetate (3×100 mL)
7. 7
   تجفيفThe combined organic layer was dried over anhydrous sodium sulfate
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated under reduced pressure
10. 10
    أخرىThe crude was purified by column chromatography over silica gel

الإجراء التجريبي

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%).

المصدر