Methyl iodide → 4-[Methyl-(2,2,2-trifluoro-acetyl)-amino]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 1970185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1970185
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:7][N:6]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:4].[C:24](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([N:10]([CH3:24])[C:11](=[O:16])[C:12]([F:15])([F:13])[F:14])[CH2:7][N:6]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:4]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 873648971,2-Pyrrolidinedicarboxylic acid, 4-[(2,2,2-trifluoroacetyl)amino]-, 1-(1,1-dimethylethyl) 2-methyl ester

Produkt 1

HCID 873659074-[Methyl-(2,2,2-trifluoro-acetyl)-amino]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4-(2,2,2-Trifluoro-acetylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.26 g, 0.76 mmol) in DMF (2 mL) was added potassium carbonate (0.139 g, 1 mmol) followed by methyl iodide (0.14 g, 1 mmol). The reaction mixture was stirred at 80° C. for 16 hours and partitioned between water and ethyl acetate. The ethyl acetate layer was washed with brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude solid. The crude solid was purified via flash chromatography (50% ethyl acetate in Hexanes) to yield the title compound.

Aufarbeitung

  1. custompartitioned between water and ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto yield a crude solid
  7. customThe crude solid was purified via flash chromatography (50% ethyl acetate in Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-81db8254b4834cd1a604db8ecfa20a77
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426604B2

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