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

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%).

1. temperaturethe mixture was then heated for 30 min in a microwave oven at 100° C
2. extractionthe mixture was extracted with ether (3×10 mL)
3. washthe ethereal phase washed with aqueous saturated NaHCO3 solution (2×10 mL)
4. dry with materialthe combined organic phases were dried over Na2SO4
5. customremoval
6. distillationby distillation
7. customof the solvent, there was obtained the crude product as a yellow oil
8. customFurther purification

ORDレコード

ord-c2185cb5aa6b4d70b4930c4a17623547

出典データセット

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07951815B2