Fumaric Acid → HCID 19095399, compound

HRID 486572Notes

Reaction equation

HRID 486572 reaction equation
[C:1]1([C:7]2[N:11]3[CH2:12][CH2:13][N:14]=[C:15]([CH3:16])[C:10]3=[CH:9][C:8]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29]>CO.O.C(O)C>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29].[C:1]1([C:7]2[N:11]3[CH2:12][CH2:13][NH:14][CH:15]([CH3:16])[C:10]3=[CH:9][C:8]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 444972Fumaric AcidHCID 4311764Sodium borohydrideHCID 19095436HCID 19095436, compound

Product 1

HCID 19095399HCID 19095399, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3,4-Dihydro-6,7-diphenyl-1-methylpyrrolo[1,2-a]pyrazine (2.0 g) was dissolved in a mixture of 100 ml of methanol and 10 ml of water under argon. The solution was treated portionwise with 0.8 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 150 ml of methylene chloride and washed with 100 ml of 10% ammonia solution. The phases were separated and the aqueous phase was extracted twice with 60 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The crude produce, 2.0 g of yellow resin, was dissolved in a 20-fold amount of ethanol and boiled briefly with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There were obtained 2.1 g (86%) of 6,7-diphenyl-1,2,3,4-tetrahydro-1-methylpyrrolo[1,2-a]pyrazine fumarate (2:1); m.pt.: 187°-190° C. (dec.).

Workup

  1. stirringstirred at room temperature overnight
  2. customThereafter, the methanol was removed in a vacuum
  3. washwashed with 100 ml of 10% ammonia solution
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted twice with 60 ml of methylene chloride each time
  6. dry with materialdried with MgSO4
  7. customThe crude produce

Sources & evidence

ORD record
ord-fcf433fb8fae4b12961ec76a9c4ea716
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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