Reaction #48320

Reaction equation

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

allyliodide

→

title compound

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

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureThe mixture was then cooled to ambient temperature
2. 2
   Filtrationfiltered through Celite
3. 3
   Washwashed with CH2Cl2
4. 4
   OtherPurification on SiO2 (10-20% EtoAc/Hexanes)

Procedure

To a solution of tert-butyl (S)-2-hydroxy-1-((S)-oxiran-2-yl)ethylcarbamate (0.125 g, 0.6 mmol; see: Kurokawa, N.; Ohfune, Y. Tetrahedron 1993, 49, 6195) in toluene (6 mL), was added allyliodide 0.3 mL, 3 mmol) followed by silver(I) oxide (0.7 g, 3 mmol). The solution was stirred at 65° C. in a darkened hood for a period of 15 h. The mixture was then cooled to ambient temperature, filtered through Celite, washed with CH2Cl2, and conc. in vacuo. Purification on SiO2 (10-20% EtoAc/Hexanes) gave the title compound as a yellow oil.

Source