4-Fluorobenzyl chloride → 1-benzyl-8-(2,4-dimethoxybenzoyl)-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5]decan-2-one

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Reaction Steps

To a solution of 8-(2,4-dimethoxybenzoyl)-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5]decan-2-one (400 mg, 1.0 mmol) in 10 mL of DMF there was added sodium hydride (40 mg, 1.5 mmol) at RT and under a blanket of nitrogen. Following stirring over a period of 1 h at RT, 4-fluorobenzyl chloride (160 mg, 1.1 mmol) was slowly added dropwise and the mixture was then heated for 30 min in a microwave oven at 100° C. Following the addition of an aqueous saturated NH4Cl solution (15 mL), the mixture was extracted with ether (3×10 mL), the ethereal phase washed with aqueous saturated NaHCO3 solution (2×10 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-(2,4-dimethoxybenzoyl)-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5]decan-2-one was obtained in a yield of 296 mg (58%).

Provenance & Evidence