反应 #157314

反应方程式

Sodium hydroxide

9-Borabicyclo[3.3.1]nonane

1-benzyl 4-tert-butyl 2-vinylpiperazine-1,4-dicarboxylate

3-bromopyridine

triphenylphosphine

→

desired product

收率 63.0%

1-benzyl 4-tert-butyl 2-(2-(pyridin-3-yl)ethyl)piperazine-1,4-dicarboxylate

收率 63.0%

反应条件

后处理

1. 1
   其他Once bubbling
2. 2
   温度the reaction mixture was heated
3. 3
   温度to reflux overnight
4. 4
   workup.ADDITIONthe reaction mixture was diluted with water (200 mL)
5. 5
   萃取extracted with EtOAc (3×200 mL)
6. 6
   干燥The combined organics were dried over Na2SO4
7. 7
   过滤filtered
8. 8
   浓缩concentrated under reduced pressure
9. 9
   其他Purification by column chomatography (10 to 40% EtOAc in Hexane gradient)

实验过程

9-Borabicyclo[3.3.1]nonane (0.5M solution in THF, 54 mL, 27 mmol) was added to 1-benzyl 4-tert-butyl 2-vinylpiperazine-1,4-dicarboxylate (2.33 g, 6.73 mmol). After 3 h, 3-bromopyridine (0.99 mL, 10.1 mmol), triphenylphosphine (0.53 g, 2.0 mmol), and tetrakis(triphenylphosphine) palladium(0) (0.311 g, 0.27 mmol) were added. Sodium hydroxide (1N aqueous solution, 16.8 mL, 16.8 mmol) was added slowly. Once bubbling ceased, the reaction mixture was heated to reflux overnight. Upon cooling to rt, the reaction mixture was diluted with water (200 mL) and extracted with EtOAc (3×200 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by column chomatography (10 to 40% EtOAc in Hexane gradient) gave 1.79 g (63%) of the desired product as a thick oil. Rf=0.57 in 80% EtOAc/Hexane. LC-MS: RT=7.69 min., [M+H]+=426.2. The material was contaminated with ˜15% triphenylphosphine, and was used without further purification.

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