Benzyl Chloride → 1-benzyl-8-(2-ethylbutyryl)-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5]decan-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-(2-ethylbutyryl)-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5]decan-2-one (420 mg, 1.3 mmol) in 20 mL of dry THF there was added sodium hydride (50 mg, 1.9 mmol) at 0° C. and under a blanket of nitrogen. Following stirring over a period of 1 h at 0° C., benzyl chloride (140 mg, 1.4 mmol) was slowly added dropwise and the mixture was then heated under reflux over a period of 24 h. Following the addition of an aqueous saturated NH4Cl solution (15 mL), the reaction mixture was isolated by filtration and the filtrate was extracted with EE (3×10 mL), and the combined organic phases were dried over Na2SO4. Following removal, by distillation, of the solvent, there was obtained the crude product as a yellow oil. Further purification was carried out by column chromatography. The product 1-benzyl-8-(2-ethylbutyryl)-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5]decan-2-one was obtained in a yield of 239 mg (45%).

Provenance & Evidence