Methanol → cis-6-cyclopropyl-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride
Reaktionsgleichung
C([N:8]1[CH2:16][C@H:15]2[C@:10]([CH3:24])([CH2:11][CH2:12][C:13]3[C:20]([CH:21]4[CH2:23][CH2:22]4)=[CH:19][CH:18]=[CH:17][C:14]=32)[CH2:9]1)C1C=CC=CC=1.CC(Cl)OC([Cl:30])=O.CO>C1(C)C=CC=CC=1>[ClH:30].[CH:21]1([C:20]2[C:13]3[CH2:12][CH2:11][C@@:10]4([CH3:24])[C@H:15]([CH2:16][NH:8][CH2:9]4)[C:14]=3[CH:17]=[CH:18][CH:19]=2)[CH2:23][CH2:22]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 160 °C
Versuchsvorschrift
cis-2-Benzyl-6-cyclopropyl-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.359 mmol, 75 mg) was dissolved in toluene (1 ml). ACE-Cl (1.654 mmol, 182 μl) was added and the reaction mixture; was heated in a microwave reactor at 160° C. for 15 minutes. MeOH (1 ml) was added and the mixture was again heated in a microwave reactor at 160° C. for 5 minutes. The resulting mixture was passed through an SCX cartridge and the resulting filtrate was concentrated in vacuo to give a crude residue that was purified by preparative-HPLC. To the pure fractions was added HCl in ether (1 ml) and the resulting solution was concentrated in vacuo to afford cis-6-cyclopropyl-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole hydrochloride (8.8 mg), m/z: 228.2 [M+H]+.
Aufarbeitung
- temperaturethe mixture was again heated in a microwave reactor at 160° C. for 5 minutes
- concentrationthe resulting filtrate was concentrated in vacuo
- customto give a crude residue that
- customwas purified by preparative-HPLC
- additionTo the pure fractions was added HCl in ether (1 ml)
- concentrationthe resulting solution was concentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-4813c960fcf740f886eab183ed5ab2ca
- Quelldatensatz
- uspto-grants-2014_05
- Patentnummer
- US08729274B2
Notizen zur Reaktion
Wird geladen…