Fumaric Acid → (R)-2-(7-methoxy-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarate

HRID 864046Notes

Reaction equation

HRID 864046 reaction equation
[N:1]([C@H:4]([CH3:20])[CH2:5][N:6]1[C:10]2=[CH:11][C:12]3[C:17]([CH2:16][CH:15]=[CH:14][C:13]=3[O:18][CH3:19])=[C:9]2[CH:8]=[N:7]1)=[N+]=[N-].[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25]>C(O)C.C(OCC)C.CO.[Pt]=O>[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25].[CH3:19][O:18][C:13]1[CH:14]=[CH:15][CH2:16][C:17]2[C:12]=1[CH:11]=[C:10]1[C:9]=2[CH:8]=[N:7][N:6]1[CH2:5][C@H:4]([NH2:1])[CH3:20]

Participants

7

Reactant 2

HCID 444972Fumaric AcidHCID 86749887(R)-1-(2-azido-propyl)-7-methoxy-1,4-dihydro-indeno[2,1-c]pyrazole

Product 1

HCID 22866135(R)-2-(7-methoxy-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarateYield 83%

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

0.5 g (1.85 mmol) of (R)-1-(2-azido-propyl)-7-methoxy-1,4-dihydro-indeno[2,1-c]pyrazole dissolved in 50 ml of anhydrous ethanol were hydrogenated over 50 mg of platinum oxide for 2 hours. The catalyst was subsequently filtered off, rinsed with ethanol and the solvent was removed in a vacuum. The colorless oil obtained was dissolved in 70 ml of anhydrous diethyl ether, filtered and treated while stirring with a solution of 215 mg(1.85 mmol) of fumaric acid in 5 ml of methanol. The mixture was stirred at room temperature for 15 hours and the white crystals were subsequently filtered off. 0.55 g (83%) of (R)-2-(7-methoxy-1,4-dihydro-indeno[2,1-c]pyrazol-1 -yl)-1-methyl-ethylamine fumarate (1:1) with m.p. 180° was obtained.

Workup

  1. filtrationThe catalyst was subsequently filtered off
  2. washrinsed with ethanol
  3. customthe solvent was removed in a vacuum
  4. customThe colorless oil obtained
  5. filtrationfiltered
  6. additiontreated
  7. filtrationthe white crystals were subsequently filtered off

Sources & evidence

ORD record
ord-c5a9390e771a4401aca99c94fcb5dc2b
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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