Fumaric Acid → HCID 67737577, compound

HRID 2396833Notes

Reaction equation

HRID 2396833 reaction equation
[N:1]([C@H:4]([CH3:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)=[N+]=[N-].[C:17]([OH:24])(=[O:23])/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21]>C(O)C.[Pt]=O>[C:17]([OH:24])(=[O:23])/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21].[F:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[N:6]([CH2:5][C@H:4]([NH2:1])[CH3:16])[CH:7]=[CH:8]2

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 54305060HCID 54305060, compound

Product 1

HCID 67737577HCID 67737577, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent2×

Procedure

A suspension of 0.1 g of platinum oxide in 25 ml of ethanol was stirred under a hydrogen atmosphere for half an hour and subsequently treated with a solution of 0.92 g of (R)-1-(2-azido-propyl)-5-fluoroindole in 25 ml of ethanol. The reaction mixture was stirred at room temperature for two hours. The catalyst was filtered off and washed with ethanol. The solution was evaporated and the residue was dissolved in 150 ml of ether and treated with 0.58 g (5 mmol) of fumaric acid and stirred overnight. The separated crystals were filtered off and dried. There were obtained 1.14 g (88%) of (R)-2-(5-fluoro-indol-1-yl)-1-methyl-ethylamine fumarate (1:1) as white crystals with m.p. 159°-161° (dec.)

Workup

  1. stirringThe reaction mixture was stirred at room temperature for two hours
  2. filtrationThe catalyst was filtered off
  3. washwashed with ethanol
  4. customThe solution was evaporated
  5. dissolutionthe residue was dissolved in 150 ml of ether
  6. stirringstirred overnight
  7. filtrationThe separated crystals were filtered off
  8. customdried

Sources & evidence

ORD record
ord-d3cea303815d4f4baa0a637a64c18e1c
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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