Reaktion #7372

Reaktionsgleichung

D-alanine tert-butylester

N,N-diisopropylethyamine

ethyl 2-azido-4-bromobutanoate

sodium iodide

→

title compound

Ausbeute 18.9%

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

Ausbeute 18.9%

Lösungsmittel

acetonitrile

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated under pressure
2. 2
   Sonstigeto give a brown oil
3. 3
   SonstigeThis oil was partitioned between DCM and water
4. 4
   WaschenThe separated organic layer was washed further with water
5. 5
   Trocknendried (over magnesium sulphate)
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe residual brown oil was purified
8. 8
   WaschenBiotage™ chromatography (silica, eluting with cyclohexane;ethyl acetate 3:1)

Vorschrift

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.

Quelle