Réaction #74436

Équation de réaction

2-((1R,2S,4R,5S)-5-hydroxybicyclo[2.2.1]heptan-2-ylamino)-5-isopropyl-5-methylthiazol-4(5H)-one

Pyridinium chlorochromate

→

title compound

5-Isopropyl-5-methyl-2-((1R,2S,4R)-5-oxobicyclo[2.2.1]heptan-2-ylamino)thiazol-4(5H)-one

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Températurethe reaction mixture was gradually warmed to ambient temperature
2. 2
   Filtrationfiltered through a pad of Celite
3. 3
   AutreThe solvents were removed in vacuo
4. 4
   Autrethe residue was purified by flash column chromatography (0 to 100% of EtOAc in hexanes)

Mode opératoire

Silica gel 60 (particle size, 0.040-0.063 mm, CAS # 63231-67-4, from EMD Chemical Inc., 2.4 g) was added to a solution of 2-((1R,2S,4R,5S)-5-hydroxybicyclo[2.2.1]heptan-2-ylamino)-5-isopropyl-5-methylthiazol-4(5H)-one (0.709 g, 2.51 mmol) in anhydrous dichloromethane (40 mL). The mixture was cooled to 0° C. Pyridinium chlorochromate (1.08 g, 5.02 mmol) was added, and the reaction mixture was gradually warmed to ambient temperature and stirred overnight. The mixture was diluted with dichloromethane, and filtered through a pad of Celite. The solvents were removed in vacuo and the residue was purified by flash column chromatography (0 to 100% of EtOAc in hexanes) to give the title compound as a tan solid.

Source