Water → (3aS)-1,2,3,3a,4,5-Hexahydropyrrolo[1,2-a]quinoxaline

HRID 1976225Notes

Reaction equation

HRID 1976225 reaction equation
[CH2:1]1[N:5]2[C:6]3[C:11]([NH:12][C:13](=O)[C@@H:4]2[CH2:3][CH2:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1>[CH2:1]1[N:5]2[C:6]3[C:11]([NH:12][CH2:13][C@@H:4]2[CH2:3][CH2:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 770113ZINC00251459HCID 21226445Aluminium lithium hydride

Product 1

HCID 13413785(3aS)-1,2,3,3a,4,5-Hexahydropyrrolo[1,2-a]quinoxalineYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.04 g of (3aS)-1,2,3,3a,4,5-hexahydro-pyrrolo[1,2-a]quinoxalin-4-one prepared in Reference Example 9 in 30 ml of anhydrous tetrahydrofuran was dropwise added, with ice-cooling, to a suspension of 0.53 g of lithium aluminum hydride in 30 ml of anhydrous tetrahydrofuran over 30 minutes. After the dropwise addition, the mixture was refluxed with heating for 2 hours. The reaction solution was ice-cooled, then 100 ml of ethyl acetate was gradually added thereto and the mixture was further stirred at room temperature for 15 hours. Water was added to the reaction liquid and the separated insolubles were filtered off through a Celite layer. The resulting organic phase was washed with water, dried over anhydrous magnesium sulfate and then concentrated. The resulting residue was subjected to silica gel column chromatography treatment and eluted with chloroform/ethyl acetate (99/1) to give 0.95 g (yield 98.1%) of the title compound.

Workup

  1. additionwas dropwise added, with ice-
  2. additionAfter the dropwise addition
  3. temperaturethe mixture was refluxed
  4. temperaturewith heating for 2 hours
  5. temperaturecooled
  6. filtrationthe separated insolubles were filtered off through a Celite layer
  7. washThe resulting organic phase was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. washeluted with chloroform/ethyl acetate (99/1)

Sources & evidence

ORD record
ord-ebbb1a87296844ea82d00a49095af589
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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