Réaction #48321

Équation de réaction

citric acid

tert-butyl (S)-2-(allyloxy)-1-((S)-oxiran-2-yl)ethylcarbamate

lithium carbonate

AcOH

→

title compound

(2S,3S)-4-(allyloxy)-3-(tert-butoxycarbonyl)-2-hydroxybutyl acetate

Solvants

DMF

DMF

Conditions de réaction

Traitement

1. 1
   Températurethen cooled to ambient temperature
2. 2
   ExtractionThe aqueous phase was extracted with EtOAc (3×20 mL)
3. 3
   Séchagethe organic extracts were dried (Na2SO4)
4. 4
   Filtrationfiltered

Mode opératoire

To a solution of lithium carbonate (0.10 g, 1.4 mmol) in DMF (2.5 mL), was added AcOH (0.078 mL, 1.4 mmol) and the solution stirred for a period of 5 min. To this mixture was added a solution of tert-butyl (S)-2-(allyloxy)-1-((S)-oxiran-2-yl)ethylcarbamate (0.11 g, 0.45 mmol) in DMF (2.5 mL). The mixture was heated to 110° C. overnight then cooled to ambient temperature. The cooled mixture was poured onto H2O and 1 N citric acid (20 mL). The aqueous phase was extracted with EtOAc (3×20 mL) and the organic extracts were dried (Na2SO4), filtered, and conc. in vacuo to afford the title compound as a yellow oil. The crude material was used without further purification. MS m/z: 326 (M+23)

Source