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

HRID 9292Notes

Reaction equation

HRID 9292 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-099d9a9db3364adcb35165d5d1ed609e
Source dataset
uspto-grants-2006_08
Patent number
US07091232B2

Reaction notes

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