Potassium Carbonate → Methyl 3-hydroxy-5-(1-methyl-2-oxopyrrolidin-3-yloxy)benzoate

HRID 75965

Reaktionsgleichung

Reaktionsgleichung von HRID 75965
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH:20]1[CH2:24][CH2:23][N:22]([CH3:25])[C:21]1=[O:26]>CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH:20]2[CH2:24][CH2:23][N:22]([CH3:25])[C:21]2=[O:26])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 75076Methyl 3,5-DihydroxybenzoateHCID 111829543-Bromo-1-methylpyrrolidin-2-one2×

Produkt 1

HCID 66971906Methyl 3-hydroxy-5-(1-methyl-2-oxopyrrolidin-3-yloxy)benzoateAusbeute 47,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of Methyl 3,5-dihydroxybenzoate (20 g) [CAS No. 2150-44-9] in dry DMF was added potassium carbonate (48 g) and the suspension stirred at ambient temperature under nitrogen. To this 3-Bromo-1-methyl-pyrrolidin-2-one (40 g) (Intermediate 5) [J. Med. Chem., 1987, 30, 1995-98] was added in three equal portions in 4 h intervals at room temperature and stirred overnight at ambient temperature. It was then quenched with water. The aqueous suspension was extracted with DCM. The to combined extracts were washed with water, brine, dried over Na2SO4, and filtered, concentrated under reduced pressure to get the thick liquid residue. The crude product was purified by column chromatography using silica gel as stationary phase and ethyl acetate: petroleum ether as a mobile phase to yield the product as white solid (15 g).

Aufarbeitung

  1. stirringstirred overnight at ambient temperature
  2. customIt was then quenched with water
  3. extractionThe aqueous suspension was extracted with DCM
  4. washwere washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto get the thick liquid residue
  9. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-caf3ec1abbe14ca7aea8bc19a5ef8617
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835469B2

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