反応 #7372

反応方程式

D-alanine tert-butylester

N,N-diisopropylethyamine

ethyl 2-azido-4-bromobutanoate

sodium iodide

→

title compound

収率 18.9%

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

収率 18.9%

溶媒

acetonitrile

acetonitrile

反応条件

後処理

1. 1
   濃縮concentrated under pressure
2. 2
   その他to give a brown oil
3. 3
   その他This oil was partitioned between DCM and water
4. 4
   洗浄The separated organic layer was washed further with water
5. 5
   乾燥dried (over magnesium sulphate)
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他The residual brown oil was purified
8. 8
   洗浄Biotage™ chromatography (silica, eluting with cyclohexane;ethyl acetate 3:1)

実験手順

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.

出典