Water → 3-(2,2-Difluoroethoxy)-1-(trifluoroacetyl)piperidin-4-one

HRID 1425164ノート

反応式

HRID 1425164 の反応式
O.[C:2](O)([C:4]([F:7])([F:6])[F:5])=[O:3].[F:9][CH:10]([F:30])[CH2:11][O:12][CH:13]1[C:18](OC)([O:19]C)[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1.C(=O)(O)[O-].[Na+]>C1COCC1>[F:30][CH:10]([F:9])[CH2:11][O:12][CH:13]1[C:18](=[O:19])[CH2:17][CH2:16][N:15]([C:2](=[O:3])[C:4]([F:7])([F:6])[F:5])[CH2:14]1

参加物

6

反応物 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86648630tert-Butyl 3-(2,2-difluoroethoxy)-4,4-dimethoxypiperidine-1-carboxylate

生成物 1

HCID 866486323-(2,2-Difluoroethoxy)-1-(trifluoroacetyl)piperidin-4-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

Water (5 mL) and TFA (2 mL) were added to a solution of tert-butyl 3-(2,2-difluoroethoxy)-4,4-dimethoxypiperidine-1-carboxylate obtained in Example (121b) (1.5 g, 4.67 mmol) in THF (30 mL), and the mixture was stirred at 70° C. for one hour. Sodium bicarbonate was added to a pH of about 8, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=10/1, 5/1, 2/1, 1/1) to obtain 1.1 g of the title compound as a light brown oily substance (86%).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=10/1, 5/1, 2/1, 1/1)

出典と根拠

ORDレコード
ord-036177182d6c433184a115a112314068
出典データセット
uspto-grants-2015_01
特許番号
US08927588B2

反応ノート

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