Benzenepropanoic acid, b-(nitromethyl)-, methyl ester → 4-苯基-2-吡咯烷酮

HRID 1045678

反应方程式

HRID 1045678 反应方程式
C[O:2][C:3](=O)[CH2:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][N+:7]([O-])=O>CO.[Ni]>[C:10]1([CH:5]2[CH2:6][NH:7][C:3](=[O:2])[CH2:4]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参与物

4

反应物 1

HCID 10537045Benzenepropanoic acid, b-(nitromethyl)-, methyl ester

产物 1

HCID 1213974-苯基-2-吡咯烷酮

试剂、催化剂与溶剂 2

HCID 935Nickel催化剂HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

实验过程

A solution of 4-nitro-3-phenyl-butyric acid methyl ester (4.02 g, 18 mmol) and Raney-Nickel (6 ml, slurry in water) in methanol (30 ml) was stirred under hydrogen atmosphere for 3 hours. After filtration using celite and removal of the solvent under reduced pressure, residue was partitioned between water and ethyl acetate. The organic layer was washed with water and brine, and then dried over sodium sulfate. The solvents were removed under reduced pressure, and the residue was dissolved in toluene (50 ml) and the resulting solution was refluxed for 6 hours. Removal of the solvent afforded crude 4-phenyl-pyrrolidin-2-one. A solution of crude 4-phenyl-pyrrolidin-2-one in tetrahydrofuran (20 ml) was added to a solution of lithium aluminum hydride (1.34 g, 35.3 mmol) and the mixture was refluxed for 6 hours. After quenching the reaction with 20% aqueous sodium hydroxide, a solution of di-tert-butyl dicarbonate (4.14 g, 19 mmol) was added and the mixture was stirred for 3 hours. Aqueous citric acid and aqueous potassium hydrogen sulfate was added to acidify the solution, and the solution was extracted with toluene. The organic layer was washed with water, aqueous sodium bicarbonate, brine, and dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified with silica gel column chromatography (eluent; hexane/ethyl acetate=9/1) to afford 1-tertbutoxycarbonyl-3-phenyl-pyrrolidine (1.84 g, 42%).

后处理

  1. filtrationAfter filtration
  2. customcelite and removal of the solvent under reduced pressure, residue
  3. customwas partitioned between water and ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvents were removed under reduced pressure
  7. dissolutionthe residue was dissolved in toluene (50 ml)
  8. temperaturethe resulting solution was refluxed for 6 hours
  9. customRemoval of the solvent

来源与证据

ORD记录
ord-b0e3f146ad0947f5a4dcbd48e84e0249
来源数据集
uspto-grants-2013_10
专利号
US08569294B2

关联笔记

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