反应 #157313

反应方程式

n-Butyl lithium

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

→

desired product

收率 76.3%

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

收率 76.3%

溶剂

THF

THF

反应条件

后处理

1. 1
   workup.WAITAfter 1 h
2. 2
   温度the reaction mixture was cooled to −78° C.
3. 3
   workup.WAITAfter 2 h
4. 4
   温度to warm to rt
5. 5
   其他was quenched with NH4Cl (saturated, aqueous solution)
6. 6
   workup.ADDITIONThe reaction mixture was diluted with water (100 mL)
7. 7
   萃取was extracted with EtOAc (3×150 mL)
8. 8
   干燥The combined organics were dried over Na2SO4
9. 9
   过滤filtered
10. 10
    浓缩concentrated under reduced pressure
11. 11
    其他Purification by column chomatography (0 to 20% EtOAc in Hexane gradient)

实验过程

n-Butyl lithium (2.5M solution in hexane, 4.0 mL, 10 mmol) was added to a suspension of methyltriphenylphosphonium bromide (4.19 g, 11.7 mmol) in THF (100 mL) at −78° C. After 10 min., the reaction mixture was allowed to warm to rt. After 1 h, the reaction mixture was cooled to −78° C., and a solution of 1-benzyl 4-tert-butyl 2-formylpiperazine-1,4-dicarboxylate (3.07 g, 8.81 mmol) in THF (10 mL) was added dropwise. After 2 h, the reaction mixture was allowed to warm to rt and was quenched with NH4Cl (saturated, aqueous solution). The reaction mixture was diluted with water (100 mL) and was extracted with EtOAc (3×150 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by column chomatography (0 to 20% EtOAc in Hexane gradient) gave 2.33 g (76%) of the desired product as a thick oil. Rf=0.35 in 30% EtOAc/Hexane. LC-MS: RT=10.1 min., [M+H]+=369.1.

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