Aluminium lithium hydride → HCID 68690614, compound

HRID 1159077Notes

Reaction equation

HRID 1159077 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C@@:14]1([CH3:22])[NH:19][C:18](=O)[CH2:17][NH:16][C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([C@:14]1([CH3:22])[CH2:15][NH:16][CH2:17][CH2:18][NH:19]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68688118HCID 68688118, compound

Product 1

HCID 68690614HCID 68690614, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1 M in THF, 7.2 ml, 7.2 mmol) was added dropwise over 15 min to a solution of (R)-3-benzyl-3-methylpiperazine-2,5-dione (0.51 g, 2.4 mmol) in THF (20 ml) stirring at ambient temperature. After stirring at reflux for 6 h, the reaction was allowed to cool to room temperature and was slowly quenched with water (0.27 ml). Sodium hydroxide (1 N, 1.0 ml) and then water (0.10 ml) were added and the gelatinous solid was filtered rinsing with THF. The filtrate was evaporated in vacuo and the residue was transferred to a separatory funnel with EtOAc. Washing the organic layer with brine and drying with MgSO4 afforded product (0.38 g) after evaporation of the solvent. This was used in the next step without further purification. MS (ESI) 191 (M+H).

Workup

  1. stirringAfter stirring
  2. temperatureat reflux for 6 h
  3. temperatureto cool to room temperature
  4. customwas slowly quenched with water (0.27 ml)
  5. additionSodium hydroxide (1 N, 1.0 ml) and then water (0.10 ml) were added
  6. filtrationthe gelatinous solid was filtered
  7. washrinsing with THF
  8. customThe filtrate was evaporated in vacuo
  9. customthe residue was transferred to a separatory funnel with EtOAc
  10. washWashing the organic layer with brine
  11. dry with materialdrying with MgSO4 afforded product (0.38 g)
  12. customafter evaporation of the solvent
  13. customThis was used in the next step without further purification

Sources & evidence

ORD record
ord-29e944bcabd54bf5a198a5a325cdd7f9
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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