Potassium Sodium Tartrate → HCID 11586806, compound

HRID 1821720Notes

Reaction equation

HRID 1821720 reaction equation
[C:1]([NH:4][C:5](=O)[CH2:6][C:7]1[C:8]([CH2:19][CH3:20])=[C:9]([C:16](=O)[CH3:17])[N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]2)(=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(OCC)C>[CH2:19]([C:8]1[C:7]([CH2:6][CH2:5][NH:4][CH2:1][CH3:2])=[C:15]2[N:10]([C:9]=1[CH2:16][CH3:17])[CH:11]=[CH:12][CH:13]=[CH:14]2)[CH3:20]

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 68982334HCID 68982334, compound

Product 1

HCID 11586806HCID 11586806, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-acetyl-2-(3-acetyl-2-ethylindolizin-1-yl)acetamide (330 mg, 1.3 mmol) isolated in Example 5 was stirred in anhydrous ethyl ether (120 mL) to which lithium aluminum hydride (330 mg) was added. The reaction mixture was heated in a nitrogen atmosphere under reflux overnight. After cooling to room temperature, Rochelle salt was added with stirring until everything dissolved. The phases were separated and the aqueous phase was extracted with ether one time. Evaporation of the organic phase gave a residue, which was purified by flash column chromatography on silica gel eluting with 3-10% methanol in methylene chloride containing 1% ammonium hydroxide. The product (110 mg) was dissolved in ethanol, treated with a solution of fumaric acid (110 mg) dissolved in ethanol and evaporated to give a residue which was recrystallized from methyl ethyl ketone. The title compound was obtained as a greenish-tan solid, mp: 154-158° C. Mass spectrum: [M+H]+ 245 m/z.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated in a nitrogen atmosphere
  3. temperatureunder reflux overnight
  4. dissolutiondissolved
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with ether one time
  7. customEvaporation of the organic phase
  8. customgave a residue, which
  9. customwas purified by flash column chromatography on silica gel eluting with 3-10% methanol in methylene chloride containing 1% ammonium hydroxide
  10. dissolutionThe product (110 mg) was dissolved in ethanol
  11. additiontreated with a solution of fumaric acid (110 mg)
  12. dissolutiondissolved in ethanol
  13. customevaporated
  14. customto give a residue which
  15. customwas recrystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-ef3edc8d71ff4d7589a447a2f58b809e
Source dataset
uspto-grants-2009_10
Patent number
US07608626B2

Reaction notes

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