반응 #591125

반응 방정식

3-Fluorothiophenol

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

DIPEA

(S)-3-(4-bromo-2-hydroxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

KHSO4 Na2SO4

→

(S)-3-[4-(3-fluoro-phenylsulfanyl)-2-hydroxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

수율 70.5%

용매

1,4-dioxane

brine

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도at reflux for 18 hours
3. 3
   추출The mixture was extracted with EtOAc
4. 4
   세척the combined organic extracts were washed with brine
5. 5
   건조dried over Na2SO4
6. 6
   여과filtered through a celite pad
7. 7
   기타evaporated under reduced pressure
8. 8
   기타The resulting crude material was purified via flash chromatography (hexane/acetone, 9/1)

실험 절차

3-Fluorothiophenol (58 μL, 0.681 mmol), Tris(dibenzylideneacetone) dipalladium(0) (77.4 mg, 0.085 mmol), 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (97.4 mg, 0.170 mmol) and DIPEA (0.156 mL, 1.71 mmol) were added to a solution of (S)-3-(4-bromo-2-hydroxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (233 mg, 0.681 mmol) in 1,4-dioxane (4.6 mL). The reaction mixture was heated at reflux for 18 hours, then cooled to 5° C. and a solution of 10% KHSO4/Na2SO4 was added, followed by brine. The mixture was extracted with EtOAc, and the combined organic extracts were washed with brine, dried over Na2SO4, filtered through a celite pad, and evaporated under reduced pressure. The resulting crude material was purified via flash chromatography (hexane/acetone, 9/1) to give 187 mg (70% yield) of (S)-3-[4-(3-fluoro-phenylsulfanyl)-2-hydroxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a white foam.

출처