반응 #157314

반응 방정식

Sodium hydroxide

9-Borabicyclo[3.3.1]nonane

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

3-bromopyridine

triphenylphosphine

→

desired product

수율 63.0%

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

수율 63.0%

반응 조건

후처리

1. 1
   기타Once bubbling
2. 2
   온도the reaction mixture was heated
3. 3
   온도to reflux overnight
4. 4
   workup.ADDITIONthe reaction mixture was diluted with water (200 mL)
5. 5
   추출extracted with EtOAc (3×200 mL)
6. 6
   건조The combined organics were dried over Na2SO4
7. 7
   여과filtered
8. 8
   농축concentrated under reduced pressure
9. 9
   기타Purification by column chomatography (10 to 40% EtOAc in Hexane gradient)

실험 절차

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.

출처