Hydrogen Peroxide → N-(4-(1,4-dihydroxy-3-methylbutyl)-3-fluorophenyl)pyridine-2-carboxamide

HRID 13427ノート

反応式

HRID 13427 の反応式
B.CSC.C1CCCCC=1.[F:11][C:12]1[CH:13]=[C:14]([NH:24][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[O:26])[CH:15]=[CH:16][C:17]=1[CH:18]([OH:23])[CH2:19][C:20]([CH3:22])=[CH2:21].[OH-:33].[Na+].OO.[Cl-].[NH4+]>O1CCCC1>[OH:23][CH:18]([C:17]1[CH:16]=[CH:15][C:14]([NH:24][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[O:26])=[CH:13][C:12]=1[F:11])[CH2:19][CH:20]([CH3:22])[CH2:21][OH:33]

参加物

8

反応物 6

HCID 784Hydrogen PeroxideHCID 8079CyclohexeneHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 23145600N-(3-fluoro-4-(1-hydroxy-3-methyl-3-buten-1-yl)phenyl)pyridine-2-carboxamide

生成物 1

HCID 23145542N-(4-(1,4-dihydroxy-3-methylbutyl)-3-fluorophenyl)pyridine-2-carboxamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

1.20 ml of borane-methyl sulfide complex (1 M dichloromethane solution) was added to a tetrahydrofuran (5 ml) solution of 0.082 ml of cyclohexene with cooling with ice. The reaction liquid was stirred for 10 minutes with cooling with ice, and a tetrahydrofuran (3 ml) solution of 301 mg of N-(3-fluoro-4-(1-hydroxy-3-methyl-3-buten-1-yl)phenyl)pyridine-2-carboxamide was added to it, and the reaction liquid was stirred at room temperature for 1 hour. 0.50 ml of aqueous 5 N sodium hydroxide solution and aqueous 35% hydrogen peroxide solution were added in order to the reaction liquid, and stirred at room temperature for 10 minutes. The reaction liquid was poured into an aqueous saturated ammonium chloride solution, extracted with ethyl acetate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=9/1) to obtain the entitled compound.

後処理

  1. temperaturewith cooling with ice
  2. customThe reaction liquid
  3. temperaturewith cooling with ice
  4. customthe reaction liquid
  5. stirringwas stirred at room temperature for 1 hour
  6. stirringstirred at room temperature for 10 minutes
  7. customThe reaction liquid
  8. extractionextracted with ethyl acetate
  9. dry with materialdried with anhydrous sodium sulfate
  10. customThe solvent was evaporated away under reduced pressure
  11. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=9/1)
  12. customto obtain the entitled compound

出典と根拠

ORDレコード
ord-fa644626d6234d1284c7cfb74c79b769
出典データセット
uspto-grants-2010_06
特許番号
US07728025B2

反応ノート

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