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

HRID 1425164노트

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HRID 1425164 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-036177182d6c433184a115a112314068
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927588B2

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