Triethylamine → 1,3-Dibenzylpyrrolidine-3-carboxylic acid amide

HRID 729448Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 729448
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:13](O)=[O:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:25]1C=CN=C1)=O.C(N(CC)CC)C.[NH4+].[OH-]>O1CCCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:13]([NH2:25])=[O:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 219793511,3-Dibenzylpyrrolidine-3-carboxylic acid

Produkt 1

HCID 219790091,3-Dibenzylpyrrolidine-3-carboxylic acid amideAusbeute 103,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 1,3-dibenzylpyrrolidine-3-carboxylic acid (Example A28, 4.0 g, 13.5 mmol), 1,1′-carbonyldiimidazole (2.42 g, 14.9 mmol), and triethylamine (2.08 mL, 14.9 mmol) in tetrahydrofuran (100 mL) is heated at reflux for 1.5 hours. The solution is cooled, poured into NH4OH (300 mL), and stirred for 18 hours. The mixture is extracted with chloroform, the organic layer is washed with water, dried, and concentrated to afford 4.13 g of the title compound as an oil; MS EI+: m/z 295 (MH+).

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 1.5 hours
  3. temperatureThe solution is cooled
  4. extractionThe mixture is extracted with chloroform
  5. washthe organic layer is washed with water
  6. customdried
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-24b354f32447486eba6b1764f5f0006f
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582627B2

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