Reaktion #157843

Reaktionsgleichung

trans-4-(tert-Butyldimethylsiloxy)-1-buten-1-ylboronic acid pinacol ester

tri(2-furyl)phosphine

cesium carbonate

(5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

→

(5R)-5-[(E)-2-{5-[(1E)-4-{[tert-butyl(dimethyl)silyl]oxy}but-1-en-1-yl]-6-methoxypyridin-2-yl}-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

Ausbeute 100.0%

Lösungsmittel

1,4-dioxane

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITThe reaction solution was left
2. 2
   Temperaturto cool
3. 3
   Filtrationfiltered through celite
4. 4
   WaschenThe filtrate was washed with brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   FiltrationAfter filtration
7. 7
   Sonstigethe solvent was evaporated under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:2)

Vorschrift

trans-4-(tert-Butyldimethylsiloxy)-1-buten-1-ylboronic acid pinacol ester (296 mg), tris(dibenzylideneacetone)dipalladium(0) (48 mg), tri(2-furyl)phosphine (73 mg) and cesium carbonate (354 mg) were added to a solution of (5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one obtained in Reference Example 4-42(1) (300 mg) in 1,4-dioxane (3 mL)-water (1 mL), and the mixture was stirred at an external temperature of 65° C. for three hours. The reaction solution was left to cool, diluted with ethyl acetate and filtered through celite. The filtrate was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:2) to give (5R)-5-[(E)-2-{5-[(1E)-4-{[tert-butyl(dimethyl)silyl]oxy}but-1-en-1-yl]-6-methoxypyridin-2-yl}-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a yellow oil (399 mg, 100%).

Quelle