Trifluoroacetic acid → Ethyl 1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxylate
Reaktionsgleichung
[CH2:1]([O:3][C:4]([C:6]1[CH:14]2[C:9](N3CCOCC3)([C:10](=[O:15])[NH:11][CH2:12][CH2:13]2)[N:8]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[N:7]=1)=[O:5])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][NH:11][C:10](=[O:15])[C:9]=2[N:8]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[N:7]=1)=[O:5])[CH3:2]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 25 °C
Versuchsvorschrift
Method B. A solution of 1-(4-methoxy-phenyl)-7a-morpholin-4-yl-7-oxo-3a,4,5,6,7,7a-hexahydro-1H-pyrazolo[3,4-c]pyridin-3-carboxylic acid ethyl ester (51, 402 mg, 1.0 mmol) in methylene chloride (CH2Cl2, 4 mL) was treated with trifluoroacetic acid (TFA, 1.0 mL) at 25° C., and the resulting reaction mixture was stirred at 25° C. for an additional 30 min. When HPLC and TLC showed the reaction was complete, the solvents were removed in vacuo. The residue was directly purified by flash column chromatography (SiO2, 5–30% EtOAc/hexane gradient elution) to afford the desired elimination product (50, 299 mg, 315 mg theoretical, 95%) as a pale-yellow oil, which solidified upon standing at room temperature in vacuo. This material was found to be identical with the product obtained from method A in every comparable aspect.
Aufarbeitung
- customthe resulting reaction mixture
- customthe solvents were removed in vacuo
- customThe residue was directly purified by flash column chromatography (SiO2, 5–30% EtOAc/hexane gradient elution)
- customto afford the desired elimination product (50, 299 mg, 315 mg theoretical, 95%) as a pale-yellow oil, which
- customupon standing at room temperature in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-175ad3f1094f46d29cc66e4971336702
- Quelldatensatz
- uspto-grants-2006_12
- Patentnummer
- US07153960B2
Notizen zur Reaktion
Wird geladen…