Reaktionsgleichung
[NH:1]1[CH2:5][CH2:4][C@@H:3]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][C@H:2]12.[Br:16][C:17]1[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>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]>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([N:1]2[CH2:5][CH2:4][C@@H:3]3[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][C@H:2]23)=[CH:19][CH:18]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 140 °C
Versuchsvorschrift
tert-Butyl(3aR,6aR)-hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (1, 1.5 g, 7.0 mmol), 1.4-dibromobenzene (2.8 g, 20.4 mmol), Pd2(dba)3 (275 mg, 0.3 mmol), BINAP (375 mg, 0.6 mmol) and sodium tert-butoxide (1.93 g, 20.0 mmol) were placed in glass microwave tubes and then purged three times with N2 gas, followed by the addition of toluene (45 mL). The mixture was heated to 140° C. for 15 minutes in a microwave reactor. The mixture was then cooled to room temperature, was filtered, and the crude mixture was purified via chromatography (SiO2, 0-25% ethyl acetate:hexanes) to provide the title compound. 1H NMR (300 MHz, CDCl3): δ=7.30 ppm (m, 2H), 7.39 (m, 2H), 4.11 (m, 1H), 3.57 (m, 3H), 3.31 (m, 3H), 2.99 (m, 1H), 2.15 (m, 1H), 1.92 (m, 1H), 1.43 (s, 9H). MS (ESI, M+1): 310.9.
Aufarbeitung
- custompurged three times with N2 gas
- additionfollowed by the addition of toluene (45 mL)
- temperatureThe mixture was then cooled to room temperature
- filtrationwas filtered
- customthe crude mixture was purified via chromatography (SiO2, 0-25% ethyl acetate:hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-922d3082846945a38837d1de7079dd7e
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07728031B2
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