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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1026632Erstellt: 26. Oktober 2026

Potassium Carbonate → cis-2-benzyl-6-cyclopropyl-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole

https://huagongshe.com/reaction/1026632

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktPotassium CarbonateHCID 11430—
EduktCyclopropylboronic acidHCID 2760897—
Eduktcis-2-benzyl-6-bromo-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindoleHCID 70664398—
KatalysatorBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
LösungsmittelWaterHCID 962—
LösungsmittelDichloromethaneHCID 6344—
Lösungsmittel1,4-DioxaneHCID 31275—
Produktcis-2-benzyl-6-cyclopropyl-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindoleHCID 7066453656,1%

Reaktionsschritte

cis-2-Benzyl-6-bromo-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.421 mmol, 150 mg) was dissolved in dioxane (2 ml) and water (0.7 ml). Cyclopropylboronic acid (0.631 mmol, 54.2 mg), 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.021 mmol, 15.40 mg) and potassium carbonate (0.631 mmol, 87 mg) were added and the reaction mixture was irradiated at 160° C. in a microwave reactor for 30 minutes. The reaction mixture was diluted with DCM and water. The phases were separated and DCM extract was concentrated in vacuo to give a crude residue that was purified by silica column chromatography (eluting with 10% EtOAc in heptane) to afford cis-2-benzyl-6-cyclopropyl-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (75 mg), m/z: 318.2 [M+H]+.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08729274B2
Quelldatensatzuspto-grants-2014_05
ORD IDord-9d6c2a1e31714e2bb438602c833072e3
Quellennotizuspto-grants-2014_05