Aluminium lithium hydride → HCID 58625894, compound

HRID 1972334Notes

Reaction equation

HRID 1972334 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][CH2:15][C@@H:16]1[NH:21][C:20](=O)[CH2:19][NH:18][C:17]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([O:14][CH2:15][C@H:16]1[CH2:17][NH:18][CH2:19][CH2:20][NH:21]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 50908773HCID 50908773, compound

Product 1

HCID 58625894HCID 58625894, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of LAH (1.87 g, 49.3 mmol) in THF (50 mL) was chilled to 0° C. To this mixture was added (3S)-3-((benzyloxy)methyl)-2,5-piperazinedione (3.85 g, 16.44 mmol) slowly portion wise. The mixture was allowed to warm to room temperature and then heated at reflux for 1 h. Afterwards, the mixture was chilled to 0° C. and the reaction was quenched with an excess of solid sodium sulfate decahydrate (approximately 50 g). After stirring at room temperature for 1 h, the mixture was filtered. The filtrate was concentrated to give (R)-2-(benzyloxymethyl)piperazine (2.60 g) as a yellow oil. To this was added excess HCl (4M in dioxane) to deliver (2R)-2-((benzyloxy)methyl)piperazine dihydrochloride.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. temperatureAfterwards, the mixture was chilled to 0° C.
  4. customthe reaction was quenched with an excess of solid sodium sulfate decahydrate (approximately 50 g)
  5. filtrationthe mixture was filtered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ec636c8bdaab4de79304e5f4e75cf79e
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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