Aluminium lithium hydride → HCID 68691037, compound

HRID 1296301Notes

Reaction equation

HRID 1296301 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:10]=1[CH2:11][N:12]1[C:25](=O)[CH:24]([CH3:27])[N:15]2[CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=3[CH2:23][C@@H:14]2[CH2:13]1>C1COCC1>[CH3:7][O:8][C:9]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:10]=1[CH2:11][N:12]1[CH2:25][CH:24]([CH3:27])[N:15]2[CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=3[CH2:23][C@@H:14]2[CH2:13]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68687822HCID 68687822, compound

Product 1

HCID 68691037HCID 68691037, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1 M in THF, 0.63 ml, 0.63 mmol) was added to a solution of (11aR)-1,2,11,11a-tetrahydro-2-(2,4-dimethoxybenzyl)-4-methyl-4H-pyrazino[1,2-b]isoquinolin-3(6H)-one (0.11 g, 0.31 mmol) in THF (1.8 ml) stirring in a room temperature bath under nitrogen. After stirring at 65° C. for 2 h, the reaction was cooled to room temperature and slowly quenched with water (0.18 ml). Sodium hydroxide (1N, 0.36 ml) followed by water (0.27 ml) were then added and the resultant gelatinous precipitate was filtered through Celite® rinsing THF. The filtrate after evaporation of the solvent was transferred to a separatory funnel with EtOAc. Washing with brine and drying with MgSO4 afforded crude product (0.10 g, 95% yield) after evaporation of the solvent. This material was used in the next step without further purification.

Workup

  1. stirringAfter stirring at 65° C. for 2 h
  2. temperaturethe reaction was cooled to room temperature
  3. customslowly quenched with water (0.18 ml)
  4. additionwere then added
  5. filtrationthe resultant gelatinous precipitate was filtered through Celite®
  6. washrinsing THF
  7. customThe filtrate after evaporation of the solvent
  8. customwas transferred to a separatory funnel with EtOAc
  9. washWashing with brine
  10. dry with materialdrying with MgSO4

Sources & evidence

ORD record
ord-9bd674bb5250481bb31b557c5cfb2857
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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