Aluminium lithium hydride → HCID 66873902, compound

HRID 249917Notes

Reaction equation

HRID 249917 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:10]=1[CH2:11][N:12]1[C@@H:21]2[C@H:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[NH:15][C:14](=O)[CH2:13]1>C1COCC1>[CH3:7][O:8][C:9]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:10]=1[CH2:11][N:12]1[C@@H:21]2[C@H:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[NH:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66874912HCID 66874912, compound

Product 1

HCID 66873902HCID 66873902, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice-cold 1.0M solution of LiAlH4 in THF (4.10 mL, 4.10 mmol) was added a solution of (4aS,8aS)-4-(2,4-dimethoxybenzyl)octahydroquinoxalin-2(1H)-one (500 mg, 1.64 mmol) in THF (10 mL). The mixture was heated at reflux for 8 h. The reaction was cooled to 0° C. and carefully quenched with EtOAc (50 mL) and 1 N NaOH solution (20 mL). The mixture stirred for 30 min and the layers were separated. The organic layer was washed with brine (20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, 0% to 60% 90:9:1 CH2Cl2/CH3OH/NH4OH in CH2Cl2) afforded (4aS,8aS)-1-(2,4-dimethoxybenzyl)decahydroquinoxaline (120.1 mg, 25.4%). 1H NMR and MS consistent.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 8 h
  3. customcarefully quenched with EtOAc (50 mL) and 1 N NaOH solution (20 mL)
  4. customthe layers were separated
  5. washThe organic layer was washed with brine (20 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification of the residue by column chromatography (silica gel, 0% to 60% 90:9:1 CH2Cl2/CH3OH/NH4OH in CH2Cl2)

Sources & evidence

ORD record
ord-29894398549d417db36606c580ec9940
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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