Ethyl Acetoacetate → t-Butyl 4-oxo-3-{[4-(trifluoromethyl)benzoyl]amino}piperidin-1-carboxylate

HRID 1360173

반응식

HRID 1360173 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[NH:15][C:16](=[O:27])[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OC(=O)CC(C)=O)C>C(Cl)Cl>[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9])[CH2:4][CH:3]1[NH:15][C:16](=[O:27])[C:17]1[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:21][CH:22]=1

참가 물질

5

반응물 3

HCID 8868Ethyl AcetoacetateHCID 159087TriacetoxyperiodinaneHCID 66969609t-Butyl 4-hydroxy-3-{[4-(trifluoromethyl)benzoyl]amino}piperidin-1-carboxylate2회

생성물 1

HCID 66969913t-Butyl 4-oxo-3-{[4-(trifluoromethyl)benzoyl]amino}piperidin-1-carboxylate수율 65%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

0.48 g (1.2 mmol) of t-butyl 4-hydroxy-3-{[4-(trifluoromethyl)benzoyl]amino}piperidin-1-carboxylate (product of step 1) was dissolved in 10 mL of methylene chloride, and 5.24 g (1.9 mmol) of Dess-Martin periodinane was dropwise added thereto. After stirring for 5 hours, 50 mL of ethylacetoacetate was dropwise added thereto, and the resulting solution was washed with water. An organic layer dried over anhydrous magnesium sulfate. The reaction solution was filtered off and distilled off under reduced pressure, then the residue was purified by column chromatography to give 0.30 g (0.78 mmol) of the title compound in a total yield of 65%.

후처리

  1. washthe resulting solution was washed with water
  2. dry with materialAn organic layer dried over anhydrous magnesium sulfate
  3. filtrationThe reaction solution was filtered off
  4. distillationdistilled off under reduced pressure
  5. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-c7d99e9e19a6411e9c098ef479236d1c
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879848B2

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