碘甲烷 → 1-苄基-3,5-二甲基哌啶-4-酮

HRID 242559笔记

反应方程式

HRID 242559 反应方程式
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16]([N-]C(C)C)(C)C.[Li+].IC>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH:12]([CH3:16])[C:11](=[O:14])[CH:10]([CH3:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参与物

5

反应物 3

HCID 6328碘甲烷HCID 5609651-苄基-3-甲基-4-哌啶酮HCID 2724682二异丙基氨基锂

产物 1

HCID 222789201-苄基-3,5-二甲基哌啶-4-酮

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

反应条件

温度
-78 °C

实验过程

To 1-benzyl-3-methyl-4-piperidone (2.0 g, 9.8 mmol) in THF at about −78° C. under argon, was added Lithium diisopropylamide (7.35 mL, 14.7 mmol, 2 M in heptane/THF/ethylbenzene). After stirring for about 1 hour at about −78° C., iodomethane (0.73 mL, 11.8 mmol) was added. The reaction mixture was stirred for about 1 hour at about −78° C., then warmed to room temperature. Stirring was continued overnight at room temperature. The reaction was quenched with saturated ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with water, then brine and dried over magnesium sulfate. The crude product was chromatographed on silica gel, eluting with EtOAc/hexane (3:10) to give a yellow oil of the title compound.

后处理

  1. stirringThe reaction mixture was stirred for about 1 hour at about −78° C.
  2. temperaturewarmed to room temperature
  3. stirringStirring
  4. waitwas continued overnight at room temperature
  5. customThe reaction was quenched with saturated ammonium chloride solution
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialbrine and dried over magnesium sulfate
  9. customThe crude product was chromatographed on silica gel
  10. washeluting with EtOAc/hexane (3:10)

来源与证据

ORD记录
ord-d139616e329d44ceabb8a5c420ff567d
来源数据集
uspto-grants-2014_02
专利号
US08653096B2

反应笔记

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