反応 #157804

反応方程式

lithiumhexamethyldisilazide

(5R)-5-[(1,3-benzothiazol-2-ylsulfonyl)methyl]pyrrolidin-2-one

water

(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)(5-chloro-6-methoxypyridin-2-yl)methanone

→

(5R)-5-[(E)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

収率 17.0%

溶媒

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGthe mixture was stirred at −78° C. for two hours
3. 3
   抽出followed by extraction with ethyl acetate
4. 4
   洗浄The organic layer was washed with brine
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   ろ過filtered
7. 7
   その他The solvent was then evaporated under reduced pressure
8. 8
   その他The residue was purified by silica gel column chromatography (chloroform:ethyl acetate=7:3→3:7)

実験手順

A 1 M solution of lithiumhexamethyldisilazide in tetrahydrofuran (35 mL) was added to a solution of (5R)-5-[(1,3-benzothiazol-2-ylsulfonyl)methyl]pyrrolidin-2-one obtained in Reference Example 3-12 (5.01 g) in tetrahydrofuran (150 mL) at −78° C. in a nitrogen gas stream, and the mixture was stirred at −78° C. for 40 minutes. A solution of (4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)(5-chloro-6-methoxypyridin-2-yl)methanone obtained in Reference Example 1-28 (3.2 g) in tetrahydrofuran (20 mL) was added, and the mixture was stirred at −78° C. for two hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:ethyl acetate=7:3→3:7) to give (5R)-5-[(E)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one as a colorless oil (688 mg, 17%).

出典