Reacción #1519122

Ecuación de reacción

TMS-triazole

Z-L-Pro-Cl

→

title compound

2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl ester

Disolventes

sulfolane

sulfolane

brine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITthe temperature is elevated to 140° C. for 3 hours
2. 2
   TemperaturaAfter the reaction mixture is cooled to rt
3. 3
   Extracciónextracted with diethyl ether
4. 4
   LavadoThe diethyl ether extracts are washed with brine
5. 5
   Secadodried over anhydrous Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated
8. 8
   OtroThe residue is purified by flash chromatography (DCM:acetone=9:1)

Procedimiento

To a solution of TMS-triazole (14.17 g, 100.3 mmol, 1 equiv.) in sulfolane (290 mL) at rt under nitrogen, is added dropwise Z-L-Pro-Cl (26.85 g, 100.3 mmol, 1 equiv.) in sulfolane (70 mL). The resulting mixture is stirred at rt for 30 minutes, then the temperature is elevated to 140° C. for 3 hours. After the reaction mixture is cooled to rt, poured into excess brine and extracted with diethyl ether. The diethyl ether extracts are washed with brine, dried over anhydrous Na2SO4, filtered and evaporated. The residue is purified by flash chromatography (DCM:acetone=9:1) to give the title compound as a light yellow oil.

Fuente