Water → 4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)pentanoic acid methyl ester

HRID 353776ノート

反応式

HRID 353776 の反応式
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH3:15])=[O:13])(OCC)=O)C.[CH3:16][C:17]([N:21]1[CH:25]=[C:24]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[N:23]=[CH:22]1)([CH3:20])[CH:18]=O.O>C1COCC1>[CH3:15][O:14][C:12](=[O:13])[CH2:11][CH2:18][C:17]([CH3:20])([N:21]1[CH:25]=[C:24]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[N:23]=[CH:22]1)[CH3:16]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 66113Methyl diethylphosphonoacetateHCID 235114292-Methyl-2-(4-pyridin-3-yl-imidazol-1-yl)-propionaldehyde

生成物 1

HCID 207376634-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)pentanoic acid methyl ester収率 75%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of sodium hydride (1.2 eq) in THF was added slowly methyl diethylphosphonoacetate (1.2 eq) at 0° C. under dry conditions and the mixture was stirred at room temperature for 30 minutes. A solution of 2-Methyl-2-(4-pyridin-3-yl-imidazol-1-yl)-propionaldehyde (1 eq), in THF was added dropwise at room temperature and the mixture was stirred for 1 hour at the same temperature. The mixture was poured into H2O and the whole was extracted with ethyl acetate. The organic layer was washed with NaCl(sat), dried over sodium sulfate, filtered and concentrated. To a solution of the residue in ethyl acetate, was added Palladium, 10 wt. % on activated carbon and left stirring under 1 atm hydrogen overnight. After the catalyst was filtered off, the filtrate was purified by flash chromatography using a solvent gradient 97% DCM, 3% MeOH and 0.1% TEA to yield 4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)pentanoic acid methyl ester (75%). MH+(274).

後処理

  1. stirringthe mixture was stirred for 1 hour at the same temperature
  2. extractionthe whole was extracted with ethyl acetate
  3. washThe organic layer was washed with NaCl(sat)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionTo a solution of the residue in ethyl acetate, was added Palladium, 10 wt. % on activated carbon
  8. waitleft
  9. stirringstirring under 1 atm hydrogen overnight
  10. filtrationAfter the catalyst was filtered off
  11. customthe filtrate was purified by flash chromatography

出典と根拠

ORDレコード
ord-baad2247e57644ae9cbe0e451745600a
出典データセット
uspto-grants-2004_06
特許番号
US06756359B2

反応ノート

読み込み中…