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

HRID 1372512ノート

反応式

HRID 1372512 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-051c2020debf4a59a6bc8f99ce07ccd5
出典データセット
uspto-grants-2007_01
特許番号
US07157604B2

反応ノート

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