Reaktionsgleichung
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][O:7][CH2:8][C:9]3[C:10]=2[C:11]=1[CH:12]=[CH:13][CH:14]=3.[CH3:15][C@@H:16]1[CH2:21][NH:20][CH2:19][CH2:18][NH:17]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:15][C@H:16]1[NH:17][CH2:18][CH2:19][N:20]([C:2]2[CH:3]=[CH:4][C:5]3[CH2:6][O:7][CH2:8][C:9]4[C:10]=3[C:11]=2[CH:12]=[CH:13][CH:14]=4)[CH2:21]1Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of 6-bromo-1H,3H-naphtho[1,8-cd]pyran (0.30 g, 1.2 mmol), 2-(R)-methylpiperazine (0.145 g, 1.44 mmol), tris(dibenzylideneacetone)dipalladium(0) (55 mg, 0.06 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (56 mg, 0.09 mmol) and sodium tert-butoxide (0.162 g, 1.68 mmol) in toluene (5 mL) was heated under reflux for 2 h. The solvent was evaporated in vacuo and the crude mixture purified by column chromatography on silica gel, eluting with dichloromethane/methanol (9:1), to yield (3R)-3-methyl-1-(1H,3H-naphtho[1,8-cd]pyran-6-yl)piperazine as an orange solid.
Aufarbeitung
- temperaturewas heated
- temperatureunder reflux for 2 h
- customThe solvent was evaporated in vacuo
- customthe crude mixture purified by column chromatography on silica gel
- washeluting with dichloromethane/methanol (9:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-3246601d97494adcb52ff263b8e80177
- Quelldatensatz
- uspto-grants-2008_02
- Patentnummer
- US07335660B2
Verknüpfte Notizen
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