Ethyl Acetate → Trans-[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanol

HRID 1639752ノート

反応式

HRID 1639752 の反応式
[CH3:1][C:2]1[CH:18]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[C:13](OCC)=[O:14])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1.O>[CH3:1][C:2]1[CH:18]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[CH2:13][OH:14])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 131729434trans-Ethyl 2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropanecarboxylate

生成物 1

HCID 66720627Trans-[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanol収率 96.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Under nitrogen atmosphere, to a solution of trans-ethyl 2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropanecarboxylate (5.40 g, 22.1 mmol) in tetrahydrofuran (150 mL) was added lithium aluminum hydride (0.750 g, 22.1 mmol) at 0° C., and the mixture was stirred for 30 min. To the reaction mixture were added ethyl acetate, water and 10% aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The extract was washed with 2 N hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by recrystallization (ethyl acetate/hexane) to give the title compound (4.30 g, yield 96%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with 2 N hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by recrystallization (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-acdfb3a474754cc0b0e2196e29fe6049
出典データセット
uspto-grants-2012_02
特許番号
US08110585B2

反応ノート

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