反応 #1106890

反応方程式

1-bromo-4-iodobenzene

caesium carbonate

BINAP

tert-butyl (2-piperidin-4-ylethyl)carbamate

→

expected product

収率 19.8%

tert-Butyl {2-[1-(4-bromo-phenyl)piperidin-4-yl]ethyl}-carbamate

収率 19.8%

溶媒

toluene

water

ethyl acetate

反応条件

後処理

1. 1
   温度The reaction mixture is then refluxed for 6 hours
2. 2
   workup.WAITthe mixture is left
3. 3
   温度at reflux for 12 hours
4. 4
   温度to cool
5. 5
   その他The aqueous phase is separated out
6. 6
   抽出extracted twice with ethyl acetate
7. 7
   洗浄the combined organic phases are washed with saturated aqueous sodium chloride solution
8. 8
   乾燥dried over sodium sulfate
9. 9
   その他After evaporating off the solvent
10. 10
    その他the residue obtained
11. 11
    その他is purified by chromatography on silica gel
12. 12
    洗浄eluting with a 98/2/0.2 mixture of dichloromethane, methanol and 28% aqueous ammonia

実験手順

6.19 g (21.90 mmol) of 1-bromo-4-iodobenzene, 5.00 g (21.90 mmol) of tert-butyl (2-piperidin-4-ylethyl)carbamate, 9.98 g (60.66 mmol) of caesium carbonate and 0.54 g (0.88 mmol) of BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) suspended in 100 mL of toluene are placed under an inert atmosphere. 0.098 g (0.44 mmol) of palladium diacetate is then added. The reaction mixture is then refluxed for 6 hours. 0.045 g (0.20 mmol) of palladium diacetate and 0.25 g (0.40 mmol) of BINAP are added and the mixture is left to stir at reflux for 12 hours. The reaction medium is allowed to cool, and ethyl acetate and water are added. The aqueous phase is separated out and extracted twice with ethyl acetate, and the combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulfate. After evaporating off the solvent, the residue obtained is purified by chromatography on silica gel, eluting with a 98/2/0.2 mixture of dichloromethane, methanol and 28% aqueous ammonia to give 1.66 g of expected product in the form of a white solid.

出典