Sodium hydride → [3S,4aR,6S,8aR]-Ethyl-6-((4-Ethoxycarbonyl-1H-Imidazol-1-yl)Methyl)-1,2,3,4,4a,5,6,7,8,8a-Decahydroisoquinoline-3-Carboxylate

HRID 1369600ノート

反応式

HRID 1369600 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][NH:9][CH:10]=1)=[O:5])[CH3:2].[H-].[Na+].[CH2:13]([O:15][C:16]([C@@H:18]1[CH2:27][C@@H:26]2[C@@H:21]([CH2:22][CH2:23][C@H:24]([CH2:28]OS(C3C=CC=C([N+]([O-])=O)C=3)(=O)=O)[CH2:25]2)[CH2:20][N:19]1C(OC)=O)=[O:17])[CH3:14]>C1COCC1>[CH2:13]([O:15][C:16]([C@@H:18]1[CH2:27][C@@H:26]2[C@@H:21]([CH2:22][CH2:23][C@H:24]([CH2:28][N:9]3[CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=[CH:8]3)[CH2:25]2)[CH2:20][NH:19]1)=[O:17])[CH3:14]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 10994514[3S,4aR,6S,8aR]-ethyl-6-((3-nitrophenylsulfonyloxy)methyl)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylateHCID 178469898HCID 178469898、化合物

生成物 1

HCID 9799112[3S,4aR,6S,8aR]-Ethyl-6-((4-Ethoxycarbonyl-1H-Imidazol-1-yl)Methyl)-1,2,3,4,4a,5,6,7,8,8a-Decahydroisoquinoline-3-Carboxylate収率 92.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Ethyl-4-imidazolecarboxylate (486 mg, 3.46 mmol) was added in portions to a slurry of sodium hydride (146 mg of a 60% mineral oil dispersion, 3.64 mmol) in THF (3.0 mL). The resulting tea-colored solution was stirred at room temperature for 55 minutes. It was then treated with [3S,4aR,6S,8aR]-ethyl-6-((3-nitrophenylsulfonyloxy)methyl)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate (1.68 g, 3.46 mmol, prepared in example 1) dissolved in THF (3.5 mL), and the reaction mixture was stirred overnight at room temperature. The reaction was then partitioned between dichloromethane (6.5 mL) and water (6.5 mL), and the layers were separated. The aqueous layer was extracted with dichloromethane (5 mL). The organic extract and organic layer were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the crude title compound. This material was purified flash chromatography (5% to 10% ethanol/toluene containing 0.5% dimethylamine, 34 g silica gel) to provide the purified intermediate title compound (1.16 g, 79%) as a colorless film.

後処理

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. customThe reaction was then partitioned between dichloromethane (6.5 mL) and water (6.5 mL)
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with dichloromethane (5 mL)
  5. extractionThe organic extract
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto provide the crude title compound
  10. customThis material was purified flash chromatography (5% to 10% ethanol/toluene containing 0.5% dimethylamine, 34 g silica gel)

出典と根拠

ORDレコード
ord-1ebf4b93d43c41f689932f55a324f7a5
出典データセット
uspto-grants-2003_06
特許番号
US06579886B2

反応ノート

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