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

HRID 1372512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1372512
[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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 210720065-Amino-2-butyl-6-fluoro-2-(3-oxopentyl)-1-indanoneAusbeute 217,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-051c2020debf4a59a6bc8f99ce07ccd5
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157604B2

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