Potassium Carbonate → 5-Difluoromethoxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

HRID 225556

Reaktionsgleichung

Reaktionsgleichung von HRID 225556
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:17])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:25]([F:32])([F:31])C(OCC)=O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:17][CH:25]([F:32])[F:31])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 67843Acetic acid, 2-chloro-2,2-difluoro-, ethyl esterHCID 18630963tert-Butyl 5-hydroxy-1,3-dihydro-2H-isoindole-2-carboxylate

Produkt 1

HCID 577532125-Difluoromethoxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl esterAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture containing 0.68 mmol 5-Hydroxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (CAS: 226070-47-9), 0.68 mmol potassium carbonate and 0.68 mmol ethyl chlorodifluoroacetate in 1.5 ml DMF was stirred overnight at 65° C. The mixture was then partitioned between ethyl acetate and water and the organic phase was then separated, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluant: n-heptane/ethylacetate) to afford the title compound as a white solid (40% yield).

Aufarbeitung

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. customthe organic phase was then separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (eluant: n-heptane/ethylacetate)

Quellen und Nachweise

ORD-Eintrag
ord-7eeace9b5415458084a6e8d730a81053
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557114B2

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