Ethyl trifluoroacetate → 4-(2,2,2-Trifluoro-acetylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 1970184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1970184
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH2:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].CCN(C(C)C)C(C)C.[F:27][C:28]([F:35])([F:34])[C:29](OCC)=[O:30]>C(OCC)(=O)C.CO>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH:10][C:29](=[O:30])[C:28]([F:35])([F:34])[F:27])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

Komponenten

6

Edukt 3

HCID 9794Ethyl trifluoroacetateHCID 81531DiisopropylethylamineHCID 49130641-Tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 873648974-(2,2,2-Trifluoro-acetylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-Amino-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (2.45 g, 10 mmol) in ethyl acetate (20 mL) and methanol (5 mL) was added DIPEA (0.15 g, 1.14 mmol) followed by ethyl trifluoroacetate (1.54 g, 11 mmol). The reaction mixture was stirred at room temperature overnight and partitioned between water and ethyl acetate. The ethyl acetate layer was washed with water, brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude solid which was used directly to the next step without further purification.

Aufarbeitung

  1. custompartitioned between water and ethyl acetate
  2. washThe ethyl acetate layer was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto yield a crude solid which
  7. customwas used directly to the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-22f80cfba487436e9a37a7acc45a328a
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426604B2

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