Triethylamine → HCID 68613368, Verbindung

HRID 1753694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1753694
[CH2:1]([O:8][C:9]([CH:11]1[CH2:15][CH2:14][C:13](=[O:16])[NH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:22][CH3:23])CC)C>ClCCl>[CH2:1]([O:8][C:9]([N:12]1[C:13](=[O:16])[CH2:14][CH2:15][CH:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[O:10])[CH2:2][CH2:3][CH:22]=[CH2:23]

Komponenten

4

Edukt 2

HCID 8471TriethylamineHCID 108474Benzyl 5-oxopyrrolidine-2-carboxylate

Produkt 1

HCID 68613368HCID 68613368, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

At 0° C., to a stirring solution of 5.5 g of 5-Oxo-pyrrolidine-2-carboxylic acid benzyl ester (25 mmol), 4 mL of triethylamine, 3.3 g of N,N-dimethylaminopyridine (27 mmol) in 40 mL of dichloromethane, was added 4.1 g of 4-pentenyl-1-yl chloroformate (27.6 mmol). The reaction mixture was then warmed to rt, and stirred over weekend. After concentration, the resulting residue was dissolved in ethyl ether 120 mL, washed with 30 mL of 1.0 N aq. HCl, brine subsequently, dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure, and the residue was purified by flash chromatography on silica gel using heptane/EtOAc (v/v 1/1), giving 7.3 g of colorless oil as intermediate 17-2 (88%). LC-MS: m/z=331.2 (ES+).

Aufarbeitung

  1. concentrationAfter concentration
  2. dissolutionthe resulting residue was dissolved in ethyl ether 120 mL
  3. washwashed with 30 mL of 1.0 N aq. HCl, brine subsequently
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe organic solvent was evaporated under reduced pressure
  6. customthe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4d3fe1ff82884de3b2975bac2e9b4bf3
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09163061B2

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