Dimethylformamide → Ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-(2-oxopropyl)cyclo-hexanecarboxylate

HRID 1944734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1944734
[CH2:1]([O:3][C:4]([C:6]1([CH2:23][CH:24]=[CH2:25])[CH2:11][CH2:10][CH:9]([N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])[CH2:8][CH2:7]1)=[O:5])[CH3:2].CN(C=[O:30])C>O.Cl.Cl[Cu].Cl[Pd]Cl>[O:21]=[C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:22])[N:12]1[CH:9]1[CH2:8][CH2:7][C:6]([CH2:23][C:24](=[O:30])[CH3:25])([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:10]1

Komponenten

7

Edukt 2

HCID 6228Dimethylformamide2×HCID 672250981-Allyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexanecarboxylic acid ethyl ester2×

Produkt 1

HCID 67225170Ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-(2-oxopropyl)cyclo-hexanecarboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24290Palladium ChlorideKatalysatorHCID 62652Cuprous chlorideKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of CuCl (147 mg, 1.484 mmol) and PdCl2 (46.1 mg, 0.26 mmol) in DMF (24 ml) and water (4 ml) was stirred under an oxygen (balloon) for 3 hours. A solution of 1-Allyl-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexanecarboxylic acid ethyl ester (Intermediate 73, 362 mg, 1.06 mmol) in DMF (16 ml) was added and the mixture was stirred at room temperature for 66 hr under O2. LCMS shows 100% conversion to product and the reaction mixture was diluted with water and 1M HCl, then extracted with ethyl acetate (×3). The organic layers were washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a yellow oil (410 mg, >100%) which was taken to the next step without further purification. LCMS [M+H]=358.3

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 66 hr under O2
  2. extractionextracted with ethyl acetate (×3)
  3. washThe organic layers were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8de3185c1a0644d3969fb81af0b6c560
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394858B2

Notizen zur Reaktion

Wird geladen…