Potassium sodium tartarate → HCID 68890454, compound

HRID 1760576Notes

Reaction equation

HRID 1760576 reaction equation
[CH3:1][C@H:2]1[N:7]2[C:8]3[C:9]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:10][CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=O)[NH:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCCC1>[CH3:1][C@H:2]1[N:7]2[C:8]3[C:9]([O:15][C:16]([F:19])([F:17])[F:18])=[CH:10][CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[CH2:5][NH:4][CH2:3]1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 69414718HCID 69414718, compound

Product 1

HCID 68890454HCID 68890454, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (R)-4-methyl-6-trifluoromethoxy-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (800 mg, 2.81 mmol) in tetrahydrofuran (4 ml.) was added to a suspension of lithium aluminium hydride (420 mg, 11.1 mmol) in tetrahydrofuran (4 mL) and the resulting mixture was heated to reflux for 90 min. After cooling the reaction mixture was slowly added to a cooled saturated aqueous sodium potassium tartrate solution. The resulting suspension was filtered on dicalite and the organics extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried (Na2SO4), and evaporated. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate to ethyl acetate/methanol gradient) to yield the title compound as a light yellow solid (385 mg, 51%). Mp: 58-60° C.; EI-MS: m/e=270.1 (M+).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 90 min
  3. temperatureAfter cooling the reaction mixture
  4. filtrationThe resulting suspension was filtered on dicalite
  5. extractionthe organics extracted twice with ethyl acetate
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate to ethyl acetate/methanol gradient)

Sources & evidence

ORD record
ord-2a986e66d561432fb3bdab700c58b4b0
Source dataset
uspto-grants-2005_01
Patent number
US06844345B2

Reaction notes

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