Réaction #990

Équation de réaction

ethyl acetate

sodium periodate

(R)-4-methyl-3-pyridin-2-yl-[1,2,3]oxathiazolidine-2-oxide

→

(R)-4-methyl-3-(2-pyridyl)-[1,2,3]oxathiazolidine-2,2-dioxide

Solvants

water

water

acetonitrile

Conditions de réaction

Traitement

1. 1
   Autrewas kept below 5° C
2. 2
   Extractionthe aqueous phase was extracted with further ethyl acetate (2×500 ml)
3. 3
   Séchagedried (MgSO4)
4. 4
   Autreevaporated in vacuo

Mode opératoire

A solution of sodium periodate (21 g, 0.10 moles) in water (150 ml) was added slowly to a solution of (R)-4-methyl-3-pyridin-2-yl-[1,2,3]oxathiazolidine-2-oxide (15.4 g, 0.78 moles) and ruthenium(III)chloride (20 mg) in acetonitrile (1540 ml) whilst the temperature was kept below 5° C. A heavy precipitate developed. The mixture was poured into a mixture of ethyl acetate (500 ml) and water (500 ml) and then shaken. The organic phase was retained and the aqueous phase was extracted with further ethyl acetate (2×500 ml). The organic phases were combined, backwashed with water (500 ml), dried (MgSO4) and then evaporated in vacuo to give (R)-4-methyl-3-(2-pyridyl)-[1,2,3]oxathiazolidine-2,2-dioxide (15.5 g) as a yellow oil which solidified on standing.

Source