Quinoline → (1R,cis)2,2-dimethyl-3-[(Z)3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylic acid

HRID 1639424노트

반응식

HRID 1639424 반응식
[H][H].[CH3:3][C:4]1([CH3:20])[C@@H:6]([C:7]#[C:8][C:9](=[O:16])[O:10][CH2:11][C:12]([F:15])([F:14])[F:13])[C@H:5]1[C:17]([OH:19])=[O:18].N1C2C(=CC=CC=2)C=CC=1>[OH-].[Pd+2].[OH-].C(OCC)(=O)C>[CH3:3][C:4]1([CH3:20])[C@@H:6](/[CH:7]=[CH:8]\[C:9](=[O:16])[O:10][CH2:11][C:12]([F:15])([F:13])[F:14])[C@H:5]1[C:17]([OH:19])=[O:18]

참가 물질

6

반응물 3

HCID 7047QuinolineHCID 13390083(1R,cis) 2,2-dimethyl-3-[3-oxo-3-(2,2,2-trifluoroethoxy)-1-propynyl]-cyclopropane-carboxylic acidHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 13390085(1R,cis)2,2-dimethyl-3-[(Z)3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylic acid수율 64.5%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 8857Ethyl Acetate용매2회

실험 절차

500 mg of 10% palladium hydroxide on barium sulfate and 5 ml of ethyl acetate were placed in a round flask connected to a hydrogen apparatus and 2 g of the product of Step C, 45 ml of ethyl acetate and 0.5 ml of quinoline were added thereto. Hydrogenation was carried out until hydrogen absorption ceased and the mixture was filtered. The filtrate was washed with N hydrochloric acid, then with water and evaporated to dryness. The 2 g of residue were chromatographed over silica gel and eluted with a 70-20-1 cyclohexane-ethyl acetate-acetic acid mixture to obtain 1.3 g of (1R,cis) 2,2-dimethyl-3-[(Z )-3-oxo-3-(2,2,2-trifluoro-ethoxy)-1-propenyl]cyclopropane-carboxylic acid.

후처리

  1. additionwere added
  2. customHydrogenation was carried out until hydrogen absorption
  3. filtrationthe mixture was filtered
  4. washThe filtrate was washed with N hydrochloric acid
  5. customwith water and evaporated to dryness
  6. customThe 2 g of residue were chromatographed over silica gel
  7. washeluted with a 70-20-1 cyclohexane-ethyl acetate-acetic acid mixture

출처 및 근거

ORD 기록
ord-56358f1ce26d4c8cb1a6414df08a65b6
출처 데이터셋
uspto-grants-1989_11
특허 번호
US04883806

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