Triethylamine → tert-Butyl (2S)-2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate

HRID 538734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 538734
[CH:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=O.C([O-])(=O)C.[NH4+:19].C([N:22](CC)[CH2:23][CH3:24])C>>[NH:19]1[CH:24]=[CH:23][N:22]=[C:1]1[C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Komponenten

4

Edukt 3

HCID 8471TriethylamineHCID 517165Ammonium AcetateHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

Produkt 1

HCID 49783269tert-Butyl (2S)-2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylateAusbeute 136,9 %

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 4 (11.09 g, 25.3 mmol), ammonium acetate (29.25 g, 38.0 mmol) and triethylamine (38.45 g, 38.0 mmol) in xylenes (600 mL) in a sealed tube was stirred at 140° C. for 2 h. After being cooled, the reaction mixture was transferred into a flask and concentrated to dryness. The residue was partitioned between chloroform and H2O, and the organic layer was washed with H2O and concentrated. The crude product was purified by silica gel column chromatography (NH4OH/acetonitrile/ethyl acetate: 1/8/100=(v/v/v)) to afford 5 (8.22 g, 75% yield) as a white solid. LC-MS (ESI): m/z 420.1 (M+H)+.

Aufarbeitung

  1. temperatureAfter being cooled
  2. customthe reaction mixture was transferred into a flask
  3. concentrationconcentrated to dryness
  4. customThe residue was partitioned between chloroform and H2O
  5. washthe organic layer was washed with H2O
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel column chromatography (NH4OH/acetonitrile/ethyl acetate: 1/8/100=(v/v/v))

Quellen und Nachweise

ORD-Eintrag
ord-c8e851cf96fe452094a34537bcb3aecf
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865756B2

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