1-Fluoro-4-(isocyanatomethyl)benzene → HCID 23122007, compound

HRID 1713523Notes

Reaction equation

HRID 1713523 reaction equation
C1(CO[C:9]([N:11]2[CH2:16][CH2:15][N:14]3[C:17](=[O:22])[O:18][C:19]([CH3:21])([CH3:20])[CH:13]3[CH2:12]2)=[O:10])C=CC=CC=1.[F:23][C:24]1[CH:33]=[CH:32][C:27]([CH2:28][N:29]=C=O)=[CH:26][CH:25]=1>C(O)C.[C].[Pd]>[F:23][C:24]1[CH:33]=[CH:32][C:27]([CH2:28][NH:29][C:9]([N:11]2[CH2:16][CH2:15][N:14]3[C:17](=[O:22])[O:18][C:19]([CH3:20])([CH3:21])[CH:13]3[CH2:12]2)=[O:10])=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 27333761-Fluoro-4-(isocyanatomethyl)benzeneHCID 23121865HCID 23121865, compound

Product 1

HCID 23122007HCID 23122007, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

(Phenylmethyl)tetrahydro-3-oxo-1,1-dimethyl-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate (0.12 g, 0.39 mmol) was dissolved in ethanol (10 mL). 10% Palladium carbon (12 mg) was added thereto, and the mixture was stirred under hydrogen atmosphere at room temperature overnight. The reaction solution was filtered through Celite, the Celite was washed with ethanol, and the filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (10 mL). 4-Fluorobenzyl isocyanate (0.20 mL, 1.6 mmol) was added thereto, and the mixture was stirred at 50° C. for 4 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:9) to obtain the title compound (0.11 g, yield 86%).

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washthe Celite was washed with ethanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in tetrahydrofuran (10 mL)
  5. stirringthe mixture was stirred at 50° C. for 4 hours
  6. concentrationThe reaction solution was concentrated under reduced pressure
  7. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1 to 1:9)

Sources & evidence

ORD record
ord-4039386156594f8f8da6761923c0380b
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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