Phenyl chloroformate → 4-(1,2,3,4,5,6-Hexahydropentalen-1-ylmethyl)-1,3-dihydro-imidazol-2-one

HRID 28751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 28751
[CH:1]1([CH2:9][C:10]2[N:11]=[CH:12][NH:13][CH:14]=2)[C:8]2[CH2:7][CH2:6][CH2:5][C:4]=2[CH2:3][CH2:2]1.C([O-])(O)=[O:16].[Na+].ClC(OC1C=CC=CC=1)=O>C1COCC1.O>[CH:1]1([CH2:9][C:10]2[NH:11][C:12](=[O:16])[NH:13][CH:14]=2)[C:8]2[CH2:7][CH2:6][CH2:5][C:4]=2[CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 178419023HCID 178419023, Verbindung

Produkt 1

HCID 219861944-(1,2,3,4,5,6-Hexahydropentalen-1-ylmethyl)-1,3-dihydro-imidazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-(1,2,3,4,5,6-hexahydro-pentalen-1-ylmethyl)-1H-imidazole; fumarate salt (Intermediate A5 as described in Example A, 340 mg, 1.81 mmol) in THF (15 mL) and water (15 mL) was treated with NaHCO3 (1.52 g, 18 mmol) at rt for 30 m. Phenyl chloroformate (600 mL, 4.7 mmol) was added and stirring was continued for 1 h at 65° C. The mixture was diluted with water (30 mL) and extracted with EtOAc (3×30 mL). The organic portions were combined and freed of solvent. The residue was dissolved in EtOH (15 mL):water (15 mL) and treated with Na2CO3 (500 mg) for 1.5 h at 95° C. The mixture was cooled to rt and the product was collected on a glass frit to give a white solid (˜50%) 4-(1,2,3,4,5,6-Hexahydro-pentalen-1-ylmethyl)-1,3-dihydro-imidazol-2-one (Compound 41).

Aufarbeitung

  1. extractionextracted with EtOAc (3×30 mL)
  2. dissolutionThe residue was dissolved in EtOH (15 mL)
  3. additionwater (15 mL) and treated with Na2CO3 (500 mg) for 1.5 h at 95° C
  4. customthe product was collected on a glass frit

Quellen und Nachweise

ORD-Eintrag
ord-c21dc13d27ca4922994f66a1bc4cc4be
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419994B2

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