Methyl Acrylate → methyl 1-chloro-8-oxo-7,8-dihydro-6H-pyrido[3,4-b]pyrrolizine-7-carboxylate

HRID 1435893Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435893
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([O:13]C)=O)[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.CC(C)([O-])C.[K+].[C:21]([O:25][CH3:26])(=[O:24])[CH:22]=[CH2:23].[NH4+].[Cl-]>C1COCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]3[N:10]([C:6]=2[CH:5]=[CH:4][N:3]=1)[CH2:23][CH:22]([C:21]([O:25][CH3:26])=[O:24])[C:11]3=[O:13]

Komponenten

7

Edukt 4

HCID 7294Methyl AcrylateHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 26599236methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

Produkt 1

HCID 77230298methyl 1-chloro-8-oxo-7,8-dihydro-6H-pyrido[3,4-b]pyrrolizine-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (12.5 g, 59 mmol) in THF (116 mL)-toluene (460 mL) were added a 1.0 M TBF solution of potassium tert-butoxide (64 mL, 64 mmol) and methyl acrylate (55 mL, 611 mmol). The resulting mixture was heated at 100° C. for 18 h. After this time, the suspension was cooled to room temperature and it was poured into a mixture of saturated aqueous NH4Cl (400 mL) and hexanes (400 mL). The solids were decanted, filtered and washed with H2O and hexanes to provide the title compound.

Aufarbeitung

  1. temperatureAfter this time, the suspension was cooled to room temperature
  2. customThe solids were decanted
  3. filtrationfiltered
  4. washwashed with H2O and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-deef35772eb84e4291fd71625942ff20
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618979B2

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