Réaction #480879

Équation de réaction

Ammonium chloride

Diisopropylethylamine

4-(R)-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one

trioxane

→

title compound

Rendement 124.2%

4-(R)-Benzyl-3-(2-(R)-hydroxymethyl-3-methylbutyryl)oxazolidin-2-one

Rendement 124.2%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was stirred for two hours, during which time the solution
2. 2
   workup.STIRRINGthe mixture was stirred for 10 min
3. 3
   Autrethe phases separated
4. 4
   Lavagethe organic layer washed with water and saturated brine
5. 5
   Séchagedried (Na2SO4)
6. 6
   Autreevaporated

Mode opératoire

Titanium tetrachloride (18 ml) was added dropwise to a solution of 4-(R)-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one (41.5 g) in dichloromethane (300 ml) at 0° C. Diisopropylethylamine (28 ml) was added dropwise and the resulting purple suspension was stirred for 30 min, then a solution of trioxane (11.2 g) was added, followed by titanium tetrachloride (18 ml) and the mixture was stirred for two hours, during which time the solution changed in colour from purple to amber. Ammonium chloride (400 ml saturated aqueous solution) was added and the mixture was stirred for 10 min, then the phases separated and the organic layer washed with water and saturated brine, dried (Na2SO4) and evaporated to give the title compound as a colourless solid (45 g).

Source