Dimethyl acetylenedicarboxylate → 7-Azabicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylic acid 2,3-dimethyl 7-tert-butyl ester

HRID 723644

Reaktionsgleichung

Reaktionsgleichung von HRID 723644
[CH3:1][O:2][C:3]([C:5]#[C:6][C:7]([O:9][CH3:10])=[O:8])=[O:4].[C:11]([O:15][C:16]([N:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>>[CH3:14][C:11]([O:15][C:16]([N:18]1[CH:19]2[CH:20]=[CH:21][CH:22]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]2[C:3]([O:2][CH3:1])=[O:4])=[O:17])([CH3:12])[CH3:13]

Komponenten

3

Edukt 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 643494tert-butyl 1H-pyrrole-1-carboxylate

Produkt 1

HCID 140854137-Azabicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylic acid 2,3-dimethyl 7-tert-butyl esterAusbeute 50 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Freshly distilled acetylenedicarboxylic acid dimethyl ester (6.7 mL, 54 mmol) and N-(tert-butyloxycarbonyl)-1H-pyrrole (9.0 mL, 54 mmol) were combined and heated at 120° C. for 3 h. Purification by flash chromatography on SiO2 eluting with EtOAc/CH2Cl2 gave 8.3 g (27 mmol, 50%) of compound 31A as a yellow solid.

Aufarbeitung

  1. customPurification by flash chromatography on SiO2 eluting with EtOAc/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-cf73406a75374ce68bddf715f69afaa4
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141578B2

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