反应 #326174

反应方程式

2-mercaptobenzoic acid

1,3-bis-(diphenylphosphino)-butane

N-[4-((S)-1-allyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethyl-benzenesulfonamide

→

product

收率 3.5%

N—((S)-4-Pyrrolidin-3-yl-phenyl)-3-trifluoromethyl-benzenesulfonamide

收率 3.5%

溶剂

tetrahydrofurane

tetrahydrofurane

反应条件

后处理

1. 1
   workup.ADDITIONwere added to the solution
2. 2
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 72 h
3. 3
   其他the solvent was evaporated
4. 4
   workup.ADDITIONdichloromethane and 1 N aqueous hydrochloric acid were added
5. 5
   萃取extracted with dichlormethane
6. 6
   洗涤the combined organic layers were washed with aqueous sodium chloride solution
7. 7
   干燥dried over sodium sulphate
8. 8
   过滤filtered
9. 9
   其他evaporated to dryness under reduced pressure
10. 10
    其他The crude product was purified via silica gel chromatography

实验过程

0.071 g of tris-(dibenzylidenaceton)-dipalladium(0) (0.08 mmol) and 0.033 g of 1,3-bis-(diphenylphosphino)-butane (0.08 mmol) were dissolved in 20 ml tetrahydrofurane and stirred for 30 min. 0.32 g of N-[4-((S)-1-allyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethyl-benzenesulfonamide (0.78 mmol), dissolved in 5 ml tetrahydrofurane, were added to the solution, followed by 0.129 g 2-mercaptobenzoic acid (0.84 mmol). The reaction mixture was stirred at room temperature for 72 h, the solvent was evaporated, and dichloromethane and 1 N aqueous hydrochloric acid were added. The aqueous phase was adjusted to basic pH, extracted with dichlormethane and the combined organic layers were washed with aqueous sodium chloride solution, dried over sodium sulphate, filtered and evaporated to dryness under reduced pressure. The crude product was purified via silica gel chromatography using a ISCO companion instrument to yield 0.01 g of product.

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