Oxalic Acid → HCID 69734306, compound

HRID 1760575Notes

Reaction equation

HRID 1760575 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]([CH3:24])=[C:13]3[C:21](=O)[NH:20][CH2:19][C@@H:18]([CH3:23])[N:14]3[C:15]=2[C:16]=1[CH3:17].[C:25]([OH:30])(=[O:29])[C:26]([OH:28])=[O:27]>C(O)C>[C:25]([OH:30])(=[O:29])[C:26]([OH:28])=[O:27].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]([CH3:24])=[C:13]3[CH2:21][NH:20][CH2:19][C@@H:18]([CH3:23])[N:14]3[C:15]=2[C:16]=1[CH3:17]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 21226445Aluminium lithium hydrideHCID 68891280HCID 68891280, compound

Product 1

HCID 69734306HCID 69734306, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Lithium aluminium hydride (64 mg, 1.67 mmol) was added in portions to a solution of (R)-7-chloro-4,6,10-trimethyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (200 mg, 0.76 mmol) and the resulting suspension was heated to reflux for 5 h. After cooling the reaction was quenched by careful addition of 1 M aqueous sodium potassium tartrate solution (20 mL). Then ether (20 mL) was added; the organic layer was separated, washed with brine, dried (Na2SO4), and evaporated. The residue was dissolved in ether (3 mL) and treated with a solution of oxalic acid (200 mg, 2.22 mmol) in ethanol (1 mL). The precipitate was collected by filtration and dried to yield the title compound (116 mg, 45%). Off-white solid. ISP-MS: m/e=249.2 ([M+H−C2H2O4]+). Anal. calc. for C16H19ClN2O4 (338.79): C 56.72; H 5.65; N 8.27; found: C 56.64; H 5.41; N 8.22.

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureto reflux for 5 h
  3. temperatureAfter cooling the reaction
  4. customwas quenched by careful addition of 1 M aqueous sodium potassium tartrate solution (20 mL)
  5. additionThen ether (20 mL) was added
  6. customthe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. dissolutionThe residue was dissolved in ether (3 mL)
  11. filtrationThe precipitate was collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-fc6bb89fda8c46c2830e021b9a5eea69
Source dataset
uspto-grants-2005_01
Patent number
US06844345B2

Reaction notes

Loading…