Sulfuric Acid → 3-(Pyridin-4-yl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine

HRID 2388698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2388698
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:11]3[CH2:12][N:13](C(=O)C)[CH2:14][CH2:15][C:10]3(N3CCCC3)[O:9][N:8]=2)=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[OH-].[Na+]>O>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:11]3[CH2:12][NH:13][CH2:14][CH2:15][C:10]=3[O:9][N:8]=2)=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 686439771-(3-(Pyridin-4-yl)-7a-(pyrrolidin-1-yl)-3a,4,7,7a-tetrahydroisoxazolo[4,5-c]pyridin-5(6H)-yl)ethanone

Produkt 1

HCID 579486603-(Pyridin-4-yl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1-(3-(Pyridin-4-yl)-7a-(pyrrolidin-1-yl)-3a,4,7,7a-tetrahydroisoxazolo[4,5-c]pyridin-5(6H)-yl)ethanone (0.63 g, 2 mmol) was initially introduced into water (14 ml) and sulfuric acid (95%, 14 ml) was added. The reaction mixture was refluxed for 5 hours, cooled with an ice bath, neutralized with sodium hydroxide solution (5 mol/l) and concentrated in vacuo. Ethyl acetate (10 ml) was added to the residue and the suspension was stirred at room temperature for 30 minutes. The precipitate was filtered out with suction and the mother liquor was extracted with ethyl acetate (4×20 ml). The combined organic phases were dried (MgSO4) and concentrated in vacuo. The yield was 0.34 g (84%). [The regiochemistry was assigned in analogy to AM1-AM4.]

Aufarbeitung

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for 5 hours
  3. temperaturecooled with an ice bath
  4. concentrationconcentrated in vacuo
  5. additionEthyl acetate (10 ml) was added to the residue
  6. filtrationThe precipitate was filtered out with suction
  7. extractionthe mother liquor was extracted with ethyl acetate (4×20 ml)
  8. dry with materialThe combined organic phases were dried (MgSO4)
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4bc3b9f4d92041139964f38864905800
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268814B2

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