Hydrochloric Acid → HCID 86697907, compound

HRID 470221Notes

Reaction equation

HRID 470221 reaction equation
C([N:4]1[CH2:11][CH:10]2[C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)([NH:7][O:8][CH2:9]2)[CH2:5]1)C=C.Cl>C(Cl)(Cl)Cl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:12]1([C:6]23[CH2:5][NH:4][CH2:11][CH:10]2[CH2:9][O:8][NH:7]3)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86697897HCID 86697897, compound

Product 1

HCID 86697907HCID 86697907, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6212ChloroformSolvent

Procedure

5-Allyl-6a-phenyl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole (3.89 g, 16.89 mmol) is dissolved in chloroform (168 mL) and the solution is degassed with dry nitrogen for 10 minutes. N,N-Dimethylbarbituric acid (13.19 g, 84.45 mmol) is added to the solution and the solution is degassed with nitrogen for another 5 min. Tetrakis(triphenylphosphine) palladium (1.95 g, 1.69 mmol) is added and the reaction is stirred for 18 hours. 1 N Hydrochloric acid (50 mL) is added and the mixture is stirred for 20 minutes. The solution is extracted with aqueous hydrochloric acid (3×75 mL) and the combined HCl solution is washed with dichloromethane. The pH is adjusted to approximately 13 with 5 N sodium hydroxide solution. The mixture is extracted with dichloromethane (3×75 mL), dried over sodium sulfate, filtered, and concentrated to give the title compound (3.21 g, 92%). EI/MS (m/e): 191.3 (M+H).

Workup

  1. customthe solution is degassed with dry nitrogen for 10 minutes
  2. customthe solution is degassed with nitrogen for another 5 min
  3. stirringthe mixture is stirred for 20 minutes
  4. extractionThe solution is extracted with aqueous hydrochloric acid (3×75 mL)
  5. washthe combined HCl solution is washed with dichloromethane
  6. extractionThe mixture is extracted with dichloromethane (3×75 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-83bcfb71fbe0402a8434cb4ae0729b33
Source dataset
uspto-grants-2014_01
Patent number
US08629270B2

Reaction notes

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