Aluminium lithium hydride → HCID 68686711, compound

HRID 1159071Notes

Reaction equation

HRID 1159071 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 68690093HCID 68690093, compound

Product 1

HCID 68686711HCID 68686711, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (1 M in THF, 4.2 ml, 4.2 mmol) was added dropwise over 15 min to a solution of (3R,6R)-1,3-dibenzyl-6-methylpiperazine-2,5-dione (0.30 g, 0.98 mmol) in THF (6.0 ml) stirring at 0° C. After stirring at 65° C. for 19 h, the reaction was allowed to cool to room temperature and was slowly quenched with water (0.40 ml). Sodium hydroxide (1 N, 0.8 ml) and then water (0.60 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 (0.28 g) after evaporation of the solvent. This was used in the next step without further purification.

Workup

  1. stirringAfter stirring at 65° C. for 19 h
  2. temperatureto cool to room temperature
  3. customwas slowly quenched with water (0.40 ml)
  4. additionSodium hydroxide (1 N, 0.8 ml) and then water (0.60 ml) were added
  5. filtrationthe gelatinous solid was filtered
  6. washrinsing with THF
  7. customThe filtrate was evaporated in vacuo
  8. customthe residue was transferred to a separatory funnel with EtOAc
  9. washWashing the organic layer with brine
  10. dry with materialdrying with MgSO4 afforded product (0.28 g)
  11. customafter evaporation of the solvent
  12. customThis was used in the next step without further purification

Sources & evidence

ORD record
ord-e2025938cd3c4448ba11327b1caf6859
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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