1-Penten-3-one → 5-Amino-2-butyl-6-fluoro-2-(3-oxopentyl)-1-indanone

HRID 1372512노트

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HRID 1372512 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])C(=O)[CH:6]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:5]2.[CH3:17][O-:18].[Na+].[CH:20]([C:22]([CH2:24][CH3:25])=[O:23])=[CH2:21]>C(O)C.C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:17](=[O:18])[C:6]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:21][CH2:20][C:22](=[O:23])[CH2:24][CH3:25])[CH2:5]2

참가 물질

6

반응물 3

HCID 153941-Penten-3-oneHCID 10942334Sodium MethoxideHCID 179727175-Amino-2-butyl-6-fluoro-1-indanone

생성물 1

HCID 210720065-Amino-2-butyl-6-fluoro-2-(3-oxopentyl)-1-indanone수율 217.4%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6344Dichloromethane용매

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온도
70 °C

실험 절차

A solution of 5-amino-2-butyl-6-fluoro-1-indanone (0.81 g, 3.84 mmol) in ethanol (18 mL) was treated with sodium methoxide (0.5M solution in MeOH, 1.54 mL, 0.768 mmol) and ethyl vinyl ketone (0.572 mL, 5.76 mmol). The resulting solution was stirred under a nitrogen atmosphere and heated in an oil bath at 70° C. over night. After cooling to room temperature, the mixture was diluted with CH2Cl2 and filtered through a pad of silica gel. The product washed off with EtOAc and the filtrate was evaporated under vacuum. The residue was purified by flash chromatography on a Biotage 40M KP-Sil column, eluting with 4:1 to 3:1 hexanes-EtOAc. The product containing fractions were evaporated under vacuum to provide to afford 5-amino-2-butyl-6-fluoro-2-(3-oxopentyl)-1-indanone(0.51 g, 45%) as a yellow foam.

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered through a pad of silica gel
  3. washThe product washed off with EtOAc
  4. customthe filtrate was evaporated under vacuum
  5. customThe residue was purified by flash chromatography on a Biotage 40M KP-Sil column
  6. washeluting with 4:1 to 3:1 hexanes-EtOAc
  7. additionThe product containing fractions
  8. customwere evaporated under vacuum
  9. customto provide

출처 및 근거

ORD 기록
ord-051c2020debf4a59a6bc8f99ce07ccd5
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157604B2

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