Reaktion #9388

Reaktionsgleichung

Phenyl chloroformate

4-(1,2,3,4,5,6-hexahydro-pentalen-1-ylmethyl)-1H-imidazole

NaHCO3

→

Compound 41

4-(1,2,3,4,5,6-Hexahydro-pentalen-1-ylmethyl)-1,3-dihydro-imidazol-2-one

Lösungsmittel

water

THF

water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle