Pyrrolidine → Dimethyl 5-(pyrrolidin-1-yl)isophthalate

HRID 1096937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096937
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])(=O)=O.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.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].COCCOC>[N:23]1([C:7]2[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=2)[C:12]([O:14][CH3:15])=[O:13])[CH2:27][CH2:26][CH2:25][CH2:24]1

Komponenten

8

Edukt 4

HCID 31268PyrrolidineHCID 62657Potassium Phosphate, TribasicHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 10617248Dimethyl 5-[[(Trifluoromethyl)sulfonyl]oxy]isophthalate

Produkt 1

HCID 57930958Dimethyl 5-(pyrrolidin-1-yl)isophthalate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a nitrogen atmosphere, a mixture of dimethyl 5-trifluoromethanesulfonyloxyisophthalate (1.37 g, 4.00 mmol), pyrrolidine (0.50 mL, 6.00 mmol), tris(dibenzylideneacetone)dipalladium(0) (37 mg, 0.040 mmol), 2-(di-tert-butylphosphino)biphenyl (24 mg, 0.080 mmol), potassium phosphate (1.19 g, 5.60 mmol) and 1,2-dimethoxyethane (12 mL) was stirred at 80° C. for 12 hours. After left cooled, the reaction mixture was diluted with ethyl acetate, filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was purified through silica gel column chromatography to obtain the title compound as a yellow solid.

Aufarbeitung

  1. waitAfter left
  2. temperaturecooled
  3. filtrationfiltered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-04d6cc786cb64d13b36840e67529af1e
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138197B2

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