1,1'-Carbonyldiimidazole → 4-{[(Imidazole-1-carbonyl)-amino]-methyl}cyclohexanecarboxylic acid methyl ester

HRID 909082

Reaktionsgleichung

Reaktionsgleichung von HRID 909082
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][NH2:12])[CH2:7][CH2:6]1)=[O:4].[C:13](N1C=CN=C1)([N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)=[O:14]>CN(C)C=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][NH:12][C:13]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[O:14])[CH2:7][CH2:6]1)=[O:4]

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 12721444(1R,4R)-Methyl 4-(aminomethyl)cyclohexanecarboxylate

Produkt 1

HCID 670955844-{[(Imidazole-1-carbonyl)-amino]-methyl}cyclohexanecarboxylic acid methyl esterAusbeute 93,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 4-aminomethyl-cyclohexanecarboxylic acid methyl ester (1.008 g, 4.758 mmol, Astatech,) in N,N-dimethyl formamide (20.0 mL) was added TEA (617 mg, 6.098 mmol) and 1,1′-carbonyldiimidazole (810.3 mg, 4.997 mmol, Aldrich,). After it was stirred at rt for 21 hrs under an argon atmosphere, the solvent was removed and the reaction mixture was extracted with EtOAc, and washed with water (2×), and saturated NaCl. The organic phase was separated, dried over Na2SO4, filtered and concentrated to give 4-{[(imidazole-1-carbonyl)-amino]-methyl}cyclohexanecarboxylic acid methyl ester (1.184 g, 4.46 mmol, 93%) which was used without further purification.

Aufarbeitung

  1. customthe solvent was removed
  2. extractionthe reaction mixture was extracted with EtOAc
  3. washwashed with water (2×), and saturated NaCl
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-20ac29ce42c7452593dadafcd749e935
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017607B2

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