Reaktion #48352

Reaktionsgleichung

ethyl 4-aminopiperidine-1-carboxylate

4-bromopyridine

sodium t-butoxide

2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

→

title compound

Ausbeute 41.1%

Ethyl 4-(pyridin-4-ylamino)piperidine-1-carboxylate

Ausbeute 41.1%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled
2. 2
   Sonstigepartitioned between ethyl acetate and water
3. 3
   WaschenThe aqueous layer was washed 3 times with methylene chloride
4. 4
   Trocknenthe combined organic layers dried over sodium sulfate
5. 5
   SonstigeThe crude product was purified by chromatography (silica gel, 0 to 10% {5% ammonium hydroxide in methanol}in methylene chloride gradient elution), which

Vorschrift

A solution of ethyl 4-aminopiperidine-1-carboxylate (2.20 g, 12.7 mmol), 4-bromopyridine (3.47 g, 17.8 mmol), sodium t-butoxide (4.54 g, 47.2 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.398 g, 0.639 mmol) and palladium acetate (0.143 g, 0.639 mmol) in toluene (40 mL) was heated at 60° C. overnight. The reaction was cooled and partitioned between ethyl acetate and water. The aqueous layer was washed 3 times with methylene chloride, and the combined organic layers dried over sodium sulfate. The crude product was purified by chromatography (silica gel, 0 to 10% {5% ammonium hydroxide in methanol}in methylene chloride gradient elution), which gave the title compound (1.3 g, 41% yield).

Quelle