Reacción #7372

Ecuación de reacción

D-alanine tert-butylester

N,N-diisopropylethyamine

ethyl 2-azido-4-bromobutanoate

sodium iodide

→

title compound

Rendimiento 18.9%

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

Rendimiento 18.9%

Disolventes

acetonitrile

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated under pressure
2. 2
   Otroto give a brown oil
3. 3
   OtroThis oil was partitioned between DCM and water
4. 4
   LavadoThe separated organic layer was washed further with water
5. 5
   Secadodried (over magnesium sulphate)
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe residual brown oil was purified
8. 8
   LavadoBiotage™ chromatography (silica, eluting with cyclohexane;ethyl acetate 3:1)

Procedimiento

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.

Fuente