Réaction #67007

Équation de réaction

N-chlorosuccinimide

butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

1-(cyclohexylmethoxy)-2-vinylbenzene

ethyl acetate

ethyl acetate

potassium hydrogencarbonate

→

tert-Butyl 4-(4-{5-[2-(cyclohexylmethoxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidine-1-carboxylate

Solvants

water

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate
2. 2
   SéchageThe organic extracts were dried over sodium sulphate
3. 3
   Concentrationconcentrated under reduced pressure
4. 4
   AutreThe residue was purified by chromatography

Mode opératoire

To a solution of tea-butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (2.90 g) and 1-(cyclohexylmethoxy)-2-vinylbenzene (2.40 g) in ethyl acetate (300 ml) were added, at room temperature, potassium hydrogencarbonate (4.60 g) and N-chlorosuccinimide (1.48 g), and then one drop of water. The reaction mixture was stirred at 60° C. for 6 h, then admixed with ethyl acetate and water and extracted with ethyl acetate. The organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave tert-butyl 4-(4-{5-[2-(cyclohexylmethoxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidine-1-carboxylate (3.40 g).

Source