Aluminium lithium hydride → HCID 68690258, compound

HRID 1159079Notes

Reaction equation

HRID 1159079 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C@H:19]([CH3:20])[C:18](=O)[NH:17][C@@H:16]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]1[CH2:15][C@@H:16]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[NH:17][CH2:18][C@@H:19]1[CH3:20])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68689339HCID 68689339, compound

Product 1

HCID 68690258HCID 68690258, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (1 M in THF, 4.8 ml, 4.8 mmol) was added dropwise over 30 min to a solution of (3S,6R)-1,3-dibenzyl-6-methylpiperazine-2,5-dione (0.39 g, 1.2 mmol) in THF (7.5 ml) stirring at 0° C. After stirring at 65° C. for 1 day, the reaction was allowed to cool to room temperature and was slowly quenched with water (0.34 ml). Sodium hydroxide (1 N, 0.68 ml) and then water (0.51 ml) were added and the gelatinous solid was filtered rinsing with THF. The filtrate was evaporated in vacuo and the residue transferred to a separatory funnel with EtOAc. Washing the organic layer with brine and drying with MgSO4 afforded product (0.40 g) after evaporation of the solvent. This was used in the next step without further purification.

Workup

  1. stirringAfter stirring at 65° C. for 1 day
  2. temperatureto cool to room temperature
  3. customwas slowly quenched with water (0.34 ml)
  4. additionSodium hydroxide (1 N, 0.68 ml) and then water (0.51 ml) were added
  5. filtrationthe gelatinous solid was filtered
  6. washrinsing with THF
  7. customThe filtrate was evaporated in vacuo
  8. customthe residue transferred to a separatory funnel with EtOAc
  9. washWashing the organic layer with brine
  10. dry with materialdrying with MgSO4 afforded product (0.40 g)
  11. customafter evaporation of the solvent
  12. customThis was used in the next step without further purification

Sources & evidence

ORD record
ord-19861f63f86c483da6cd60adb2c607df
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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