氢化钠 → 1-(4-Pyridyl)-3-(5-nitro-2-pyridyloxy)pyrrolidine

HRID 346681

反应方程式

HRID 346681 反应方程式
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]2)=[CH:5][CH:4]=1.Br[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][CH:11]([O:14][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=3)[CH2:10]2)=[CH:5][CH:4]=1

参与物

5

反应物 3

HCID 24758氢化钠HCID 782402-溴-5-硝基吡啶HCID 219061981-(Pyridin-4-yl)pyrrolidin-3-ol

产物 1

HCID 183571081-(4-Pyridyl)-3-(5-nitro-2-pyridyloxy)pyrrolidine

试剂、催化剂与溶剂 1

HCID 74236四丁基溴化铵催化剂

实验过程

Sodium hydride (60% dispersion in paraffin oil, 146 mg) 1.2 equivalent) was added to an oven-dried round-bottomed flask and washed under an argon atmosphere with pentane. DMF (5 ml) was then added, followed by 1-(4-pyridyl)-3-hydroxypyrrolidine (1.0 equivalent, 3.05 mmol) and tetra-n-butylammonium bromide (59 mg, 0.18 mmol). The mixture was added as a slurry to 2-bromo-5-nitropyridine (1.5 equivalent) in a second dry flask under argon, with stirring. After the reaction was complete the solvent was evaporated under vacuum. The residue was purified by chromatography on silica, eluting from 1%MeOH/1%NH4OH/CH2Cl2 to 10%MeOH/1%NH4OH/CH2Cl2 (in 1% increments). The crude product was recrystallised from EtOAc to give 1-(4-pyridyl)-3-(5-nitro-2-pyridyloxy)pyrrolidine as a pale brown solid (460 mg);

后处理

  1. washwashed under an argon atmosphere with pentane
  2. additionDMF (5 ml) was then added
  3. customwas evaporated under vacuum
  4. customThe residue was purified by chromatography on silica
  5. washeluting from 1%MeOH/1%NH4OH/CH2Cl2 to 10%MeOH/1%NH4OH/CH2Cl2 (in 1% increments)
  6. customThe crude product was recrystallised from EtOAc

来源与证据

ORD记录
ord-5f82f0d21b16461baaf51b1e0584d208
来源数据集
uspto-grants-2007_02
专利号
US07173025B1

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