Sodium hydride → 1-(4-Pyridyl)-3-(5-nitro-2-pyridyloxy)pyrrolidine

HRID 346681

反応式

HRID 346681 の反応式
[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

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 782402-Bromo-5-nitropyridineHCID 219061981-(Pyridin-4-yl)pyrrolidin-3-ol

生成物 1

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

試薬・触媒・溶媒 1

HCID 74236Tetrabutylammonium Bromide触媒

実験手順

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);

後処理

  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

出典と根拠

ORDレコード
ord-5f82f0d21b16461baaf51b1e0584d208
出典データセット
uspto-grants-2007_02
特許番号
US07173025B1

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