反応 #748714

反応方程式

3-(methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

tert-Butyllithium

4-bromo-1,2-dichlorobenzene

→

3-(3,4-dichloro-benzoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

収率 22.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction mixture was stirred at −78° C. for 20 minutes
2. 2
   温度warmed up to room temperature over a period of 30 minutes
3. 3
   その他The reaction was quenched by addition of saturated aqueous NH4Cl
4. 4
   workup.ADDITIONdiluted with water
5. 5
   抽出extracted with EtOAc
6. 6
   乾燥The combined organic extracts were dried over MgSO4
7. 7
   ろ過filtered
8. 8
   その他evaporated under reduced pressure
9. 9
   その他to give an oil that
10. 10
    その他was purified by flash chromatography (10% to 30% of EtOAc in hexane)

実験手順

tert-Butyllithium (1.7 M in pentane, 2.5 mL, 4.25 mmol) was added at −78° C. to a solution of 4-bromo-1,2-dichlorobenzene (435 mg, 1.93 mmol) in THF (10 mL) under nitrogen atmosphere. The resulting solution was stirred at −78° C. for 15 minutes, and then a solution of 3-(methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (500 mg, 1.93 mmol) in THF (2 mL) was slowly added. The reaction mixture was stirred at −78° C. for 20 minutes and then warmed up to room temperature over a period of 30 minutes. The reaction was quenched by addition of saturated aqueous NH4Cl, then diluted with water and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and evaporated under reduced pressure to give an oil that was purified by flash chromatography (10% to 30% of EtOAc in hexane) to give 143 mg (22% yield) of 3-(3,4-dichloro-benzoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a colorless oil.

出典