Réaction #53896

Équation de réaction

NaHCO3

trans-N-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide

imidazole

TBDMSCl

→

trans-N-[4-(5-{[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-ethyl-amino}-pentyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide

Rendement 10.2%

Solvants

DMF

toluene

Conditions de réaction

Traitement

1. 1
   Autreevaporated (3×)
2. 2
   workup.DISSOLUTIONredissolved in lml DMF
3. 3
   Extractionextracted with ether
4. 4
   LavageThe organic layer was washed with water and brine
5. 5
   Séchagedried over Na2SO4

Mode opératoire

400 mg (8.4 mmol) trans-N-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide were suspended in toluene and evaporated (3×), redissolved in lml DMF and treated with 102.4 mg (1.5 mmol, 1.8 eq) imidazole. At 0° C., 176 mg (11.7 mmol, 1.4 eq) TBDMSCl in 2 ml DMF were added, and the reaction mixture was stirred at 50° C. for 1 h. The solution was added to an aqueous solution of NaHCO3 and extracted with ether. The organic layer was washed with water and brine, and dried over Na2SO4. 509 mg crude trans-N-[4-(5-{[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-ethyl-amino}-pentyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide were isolated as light yellow oil.

Source