Fumaric Acid → HCID 19095434, compound

HRID 486587Notes

Reaction equation

HRID 486587 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[CH:9][C:10]3[C:18]4[N:17]5[CH2:19][CH2:20][N:21]=[C:22]([CH3:23])[C:16]5=[CH:15][C:14]=4[CH2:13][CH2:12][C:11]=3[CH:24]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31]>CO.O.C(O)C>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[CH:1]1([O:6][C:7]2[CH:8]=[CH:9][C:10]3[C:18]4[N:17]5[CH2:19][CH2:20][NH:21][CH:22]([CH3:23])[C:16]5=[CH:15][C:14]=4[CH2:13][CH2:12][C:11]=3[CH:24]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 3

HCID 444972Fumaric AcidHCID 4311764Sodium borohydrideHCID 19095278HCID 19095278, compound

Product 1

HCID 19095434HCID 19095434, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-Cyclopentyloxy-5,6,10,11-tetrahydro-8-methylbenzo[g]pyrazino[1,2-a]indole (0.8 g) was dissolved in a mixture of 50 ml of methanol and 5 ml of water under argon. The solution was treated portionwise with 0.3 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 30 ml of methylene chloride and washed with 50 ml of 10% ammonia solution. The phases were separated and the aqueous phase was extracted twice with 30 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 0.8 g of amorphous, brown solid, was chromatographed on 30 g of silica gel with methylene chloride/methanol mixtures (50:1 to 20:1). The isolated crude product was dissolved in a 25-fold amount of hot ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 0.34 g (31 %) of 3-cyclopentyloxy-5,6,8,9,10,11-hexahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole fumarate (2:1); m.pt.: 187°-189° C. (dec.).

Workup

  1. stirringstirred at room temperature overnight
  2. customThereafter, the methanol was removed in a vacuum
  3. washwashed with 50 ml of 10% ammonia solution
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted twice with 30 ml of methylene chloride each time
  6. dry with materialdried with MgSO4
  7. customThe residue, 0.8 g of amorphous, brown solid, was chromatographed on 30 g of silica gel with methylene chloride/methanol
  8. customThe isolated crude product

Sources & evidence

ORD record
ord-7b5be6f959604c73af21398de97b7835
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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