Reaktion #157858

Reaktionsgleichung

ammonium chloride

benzylzinc(II) bromide

tri(2-furyl)phosphine

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

→

(5R)-5-[(E)-2-(5-benzyl-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionfollowed by extraction with ethyl acetate
2. 2
   TrocknenThe organic layer was dried over sodium sulfate
3. 3
   Sonstigethe solvent was evaporated under reduced pressure
4. 4
   SonstigeThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:0)

Vorschrift

0.05 M benzylzinc(II) bromide (385 μL), tris(dibenzylideneacetone)dipalladium(0) (8.0 mg) and tri(2-furyl)phosphine (15 mg) were added to a solution of (5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one obtained in Reference Example 4-42(2) (30 mg) in tetrahydrofuran (2 mL), and the mixture was stirred under microwave irradiation at 110° C. for one hour. An ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:0) to give (5R)-5-[(E)-2-(5-benzyl-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one (23 mg).

Quelle