Reaktion #969896

Reaktionsgleichung

phenyl boronic acid

potassium phosphate

1,4-dioxane

4-[1-(4-bromophenyl)cyclopropyl]-1-(adamantan-2-yl)-3,3-dimethylazetidin-2-one

4-[1-(4-bromophenyl)cyclopropyl]-1-(adamantan-2-yl)-3,3-dimethylazetidin-2-one

water

→

4-[1-(biphenyl-4-yl)cyclopropyl]-1-(adamantan-2-yl)-3,3-dimethylazetidin-2-one

Ausbeute 84.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
3. 3
   Einengenconcentrated in vacuo
4. 4
   SonstigeThe obtained residue was purified

Vorschrift

A solution of 4-[1-(4-bromophenyl)cyclopropyl]-1-(adamantan-2-yl)-3,3-dimethylazetidin-2-one (12.2 mg, 0.0285 mmol) in 1,4-dioxane (3 mL) prepared in Example 75 was added with tetrakis(triphenylphosphine) palladium (1.6 mg, 1.4 μmol), phenyl boronic acid (7 mg, 0.057 mmol), and potassium phosphate (30 mg, 0.142 mmol) at room temperature, and the resultant was stirred at 100° C. for 20 hours. The reaction solution was poured into water, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using thin-layer chromatography (hexane:ethyl acetate=3:1), and 4-[1-(biphenyl-4-yl)cyclopropyl]-1-(adamantan-2-yl)-3,3-dimethylazetidin-2-one (10.2 mg, 84%) was obtained as a white amorphous solid.

Quelle