Cyclopentanone → 5H-Cyclopenta[c]pyridine-1-carboxylicacid,6,7-dihydro-,ethylester(9CI)

HRID 575846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 575846
N1[CH:6]=[CH:5][N:4]=[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])N=1.[C:12]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13]1.N1CCCC1>C1(C)C=CC=CC=1>[C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:13]2[CH2:14][CH2:15][CH2:16][C:12]=2[CH:6]=[CH:5][N:4]=1

Komponenten

5

Edukt 3

HCID 8452CyclopentanoneHCID 31268PyrrolidineHCID 12559180Ethyl [1,2,4]triazine-3-carboxylate

Produkt 1

HCID 450986655H-Cyclopenta[c]pyridine-1-carboxylicacid,6,7-dihydro-,ethylester(9CI)Ausbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Ethyl 1,2,4-triazine-3-carboxylate (7 g, 45.8 mmol), cyclopentanone (4.9 mL, 55.0 mmol), and pyrrolidine (4.6 mL, 55.0 mmol) in toluene (100 mL) were heated to reflux for 12 h. The mixture was purified by column on silica gel chromatography (PE/EtOAc=5:1) to give the title compound (2.02 g, 25%) as a brown oil. LCMS: 192 (M+1)+

Aufarbeitung

  1. temperatureto reflux for 12 h
  2. customThe mixture was purified by column on silica gel chromatography (PE/EtOAc=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-89c18a4837e349e69afab6a135847481
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034900B2

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