Fumaric Acid → HCID 19095377, compound

HRID 486564Notes

Reaction equation

HRID 486564 reaction equation
[CH:1]1([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:17]4[CH2:18][CH2:19][N:20]=[C:21]([CH3:22])[C:16]4=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29]>CO.O.C(Cl)Cl.C(O)C>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29].[CH:1]1([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:17]4[CH2:18][CH2:19][NH:20][CH:21]([CH3:22])[C:16]4=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

8

Reactant 3

HCID 444972Fumaric AcidHCID 4311764Sodium borohydrideHCID 19095325HCID 19095325, compound

Product 1

HCID 19095377HCID 19095377, compoundYield 66%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

6-[p-(Cyclopentyloxy)phenyl]-3,4-dihydro-1-methylpyrrolo[1,2-a]pyrazine (1.5 g) was dissolved in a mixture of 100 ml of methanol, 10 ml of water and 25 ml of methylene chloride under argon. The solution was treated portionwise with 0.6 g of sodium borohydride while stirring and stirred at room temperature overnight. Thereafter, the solvent was removed in a vacuum, the residue was taken up in 100 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 product, 1.6 g of brown oil, was dissolved in a 20-fold amount of hot ethanol and treated while hot with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 1.2 g (66%) of 6-[p-(cyclopentyloxy)phenyl]-1,2,3,4-tetrahydro-1-methylpyrrolo[1,2-a]pyrazine fumarate (2:1); m.pt.: 172°-174° C. (dec.).

Workup

  1. stirringstirred at room temperature overnight
  2. customThereafter, the solvent 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. dissolutionThe crude product, 1.6 g of brown oil, was dissolved in a 20-fold amount of hot ethanol

Sources & evidence

ORD record
ord-34c75a78bfed4cf9a2b5db3768efe109
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

Loading…