Ethyl Acetate → cis-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine

HRID 455349Notes

Reaction equation

HRID 455349 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:12](=O)[CH2:11][CH2:10][C@@H:9]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[CH2:20][C@H:8]12.[OH-].[Na+].C(OCC)(=O)C>O1CCCC1>[NH:7]1[CH2:12][CH2:11][CH2:10][C@@H:9]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[CH2:20][C@H:8]12

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58124040cis-1,3,4,4a,9,9a-Hexahydro-indeno[2,1-b]pyridin-2-one

Product 1

HCID 58123900cis-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1 mol/L in tetrahydrofuran, 12 mL) is added to a solution of cis-1,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-2-one (0.95 g) in tetrahydrofuran (15 mL) at room temperature. The resulting solution is heated to reflux temperature and stirred at this temperature for 2 h. After cooling to room temperature, the solution is poured into ice-cold water, 1 M aqueous NaOH solution and ethyl acetate are added, and the resulting mixture is filtered over Celite. The aqueous phase of the filtrate is separated and extracted with ethyl acetate and the extracts are combined with the organic phase of the filtrate. The organic phase is washed with brine and dried (MgSO4). The solvent is evaporated to give the title compound as a colorless solid. Yield: 0.83 g (94% of theory); LC (method 1): tR=1.29 min; Mass spectrum (ESI+): m/z=174 [M+H]+.

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureto reflux temperature
  3. additionare added
  4. filtrationthe resulting mixture is filtered over Celite
  5. customThe aqueous phase of the filtrate is separated
  6. extractionextracted with ethyl acetate
  7. washThe organic phase is washed with brine
  8. dry with materialdried (MgSO4)
  9. customThe solvent is evaporated

Sources & evidence

ORD record
ord-ca52aa7c55054e8d86a460d501058ad6
Source dataset
uspto-grants-2013_07
Patent number
US08497281B2

Reaction notes

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