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

HRID 864036Notes

Reaction equation

HRID 864036 reaction equation
[N:1]([C@@H:4]([CH3:21])[CH2:5][N:6]1[C:10]2=[CH:11][C:12]3[C:17]([C:16]([CH3:19])([CH3:18])[CH:15]=[CH:14][C:13]=3[CH3:20])=[C:9]2[CH:8]=[N:7]1)=[N+]=[N-].[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26]>CO.C(OCC)C.[Pt]=O>[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26].[CH3:19][C:16]1([CH3:18])[C:17]2[C:12]([CH:11]=[C:10]3[C:9]=2[CH:8]=[N:7][N:6]3[CH2:5][C@@H:4]([NH2:1])[CH3:21])=[C:13]([CH3:20])[CH:14]=[CH:15]1

Participants

6

Reactant 2

HCID 444972Fumaric AcidHCID 54469999(S)-1-(2-azido-propyl)-4,4,7-trimethyl-1,4-dihydro-indeno[2,1-c]pyrazole

Product 1

HCID 86749883(S)-2-(4,4,7-trimethyl-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarateYield 54%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

0.7 g (2.5 mmol) of (S)-1-(2-azido-propyl)-4,4,7-trimethyl-1,4-dihydro-indeno[2,1-c]pyrazole dissolved in 50 ml of anhydrous methanol was hydrogenated over 70 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 290 mg (2.5 mmol) of fumaric acid in 5 ml of methanol. The mixture was stirred at room temperature for 4 hours and the white crystals were subsequently filtered off. 0.5 g (54%) of (S)-2-(4,4,7-trimethyl-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-1-methyl-ethylamine fumarate (1:1) with m.p. 158° 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-78e4d8e1617b4a41b017b09fdd2e3626
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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