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Methanol → Carbonic acid 1-(4-ethyl-phenyl)-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl ester methyl ester

HRID 1835289
ノート
印刷プレビュー

反応式

HRID 1835289 の反応式
[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH2:16]([C:18]1[CH:23]=[CH:22][C:21]([CH:24]2[CH2:26][O:25]2)=[CH:20][CH:19]=1)[CH3:17].[C:27](N1C=CN=C1)(N1C=CN=C1)=[O:28].[CH3:39][OH:40]>C(O)(C)C.O>[CH3:39][O:40][C:27](=[O:28])[O:25][CH:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:16][CH3:17])=[CH:23][CH:22]=1)[CH2:26][N:11]1[CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:15][CH:14]=2)[CH2:9][CH2:10]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 887MethanolHCID 682631,1'-CarbonyldiimidazoleHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 103745952-(4-Ethylphenyl)-oxirane

生成物 1

HCID 11742469Carbonic acid 1-(4-ethyl-phenyl)-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl ester methyl ester

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 3776Isopropanol溶媒

実験手順

A mixture of 4-(4-fluorobenzoyl)piperidine (5 mmol) and 2-(4-ethylphenyl)-oxirane (5 mmol) was refluxed in 30 ml of isopropanol for 4 h. This solution was then concentrated on a rotary evaporator and diluted with ethyl acetate. This mixture was then washed with brine, the resulting organic layer was dried and concentrated in vacuo. The crude product was dissolved in THF (50 ml) and was added with 1,1′-carbonyl diimidazole (2 mmol) at 0° C. The reaction mixture was stirred at room temperature for 4 h, followed by the addition of excess methanol (10 ml) at 0° C. After 5 h stirring at room temperature, water was added to terminate the reaction. The organic layer was extracted 3 times with dichloromethane, dried and concentrated in vacuo. The resulting carbonic acid 1-(4-ethyl-phenyl)-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl ester methyl ester was obtained by column chromatography.

後処理

  1. concentrationThis solution was then concentrated on a rotary evaporator
  2. additiondiluted with ethyl acetate
  3. washThis mixture was then washed with brine
  4. customthe resulting organic layer was dried
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude product was dissolved in THF (50 ml)
  7. stirringAfter 5 h stirring at room temperature
  8. customto terminate
  9. customthe reaction
  10. extractionThe organic layer was extracted 3 times with dichloromethane
  11. customdried
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-90d2bda0f6204f3aabef9bc568a8f257
出典データセット
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06770659B2

反応ノート

読み込み中…

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