반응 #7372

반응 방정식

D-alanine tert-butylester

N,N-diisopropylethyamine

ethyl 2-azido-4-bromobutanoate

sodium iodide

→

title compound

수율 18.9%

tert-Butyl (2R)-2-(3-azido-2-oxopyrrolidin-1-yl)propanoate

수율 18.9%

용매

acetonitrile

acetonitrile

반응 조건

후처리

1. 1
   농축concentrated under pressure
2. 2
   기타to give a brown oil
3. 3
   기타This oil was partitioned between DCM and water
4. 4
   세척The separated organic layer was washed further with water
5. 5
   건조dried (over magnesium sulphate)
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residual brown oil was purified
8. 8
   세척Biotage™ chromatography (silica, eluting with cyclohexane;ethyl acetate 3:1)

실험 절차

To a solution of D-alanine tert-butylester (1.28 g) and N,N-diisopropylethyamine (1.22 ml) in acetonitrile (15 ml), was added a solution of ethyl 2-azido-4-bromobutanoate (1 g) and sodium iodide (0.02 g) in acetonitrile (5 ml). The mixture was heated at 60° C. for 60 h and then concentrated under pressure to give a brown oil. This oil was partitioned between DCM and water. The separated organic layer was washed further with water and dried (over magnesium sulphate), and concentrated under reduced pressure. The residual brown oil was purified using Biotage™ chromatography (silica, eluting with cyclohexane;ethyl acetate 3:1) to give the title compound (0.204 g) as a mixture of two diastereoisomers.

출처