Fumaric Acid → HCID 19095345, compound

HRID 486561Notes

Reaction equation

HRID 486561 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)=[CH:9][CH:10]=2)[CH2:5][CH2:6][N:7]=1.[BH4-].[Na+].[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27]>CO.O.C(O)C>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][CH:12]=3)=[CH:9][CH:10]=[C:3]12

Participants

7

Reactant 3

HCID 444972Fumaric AcidHCID 4311764Sodium borohydrideHCID 19095294HCID 19095294, compound

Product 1

HCID 19095345HCID 19095345, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3,4-Dihydro-1-methyl-6-[4-(trifluoromethyl)-phenyl]pyrrolo[1,2-a]pyrazine (2.5 g) was dissolved in a mixture of 130 ml of methanol and 13 ml of water under argon. The solution was treated portionwise with 1.0 g of sodium borohydride while stirring and stirred at room temperature overnight. Thereafter, the methanol was removed in a vacuum, the residue was taken up in 100 ml of methylene chloride and washed with 80 ml of 10% ammonia solution. The phases were separated and the aqueous phase was extracted twice with 50 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The crude product, 2.5 g of yellow-brown solid, was dissolved in a 20-fold amount of ethanol, treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol and concentrated to 40 ml. There were obtained 2.5 g (70%) of 1,2,3,4-tetrahydro-1-methyl-6-[4-(trifluoromethyl)phenyl]pyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt.: 180°-183° C. (dec.).

Workup

  1. stirringstirred at room temperature overnight
  2. customThereafter, the methanol was removed in a vacuum
  3. washwashed with 80 ml of 10% ammonia solution
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted twice with 50 ml of methylene chloride each time
  6. dry with materialdried with MgSO4
  7. dissolutionThe crude product, 2.5 g of yellow-brown solid, was dissolved in a 20-fold amount of ethanol
  8. concentrationconcentrated to 40 ml

Sources & evidence

ORD record
ord-5cfaaadb323f41b6ac6c2ba6f856a9e3
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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