Aluminium lithium hydride → HCID 86679684, compound

HRID 577758Notes

Reaction equation

HRID 577758 reaction equation
[CH2:1]([N:8]1[CH2:12][C@:11]2([OH:18])[C:13](=O)[NH:14][C:15](=O)[C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:12][C@:11]2([OH:18])[C@@H:10]([CH2:15][NH:14][CH2:13]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86679683HCID 86679683, compound

Product 1

HCID 86679684HCID 86679684, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (cis)-5-benzyl-3a-hydroxytetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione (450 mg, 1.83 mmol) in THF (9 mL) under nitrogen, was added LAH (9.42 mL, 1.0 M in diethyl ether) to form a white suspension. The resulting mixture was stirred at ambient temperature for 21 hrs. The reaction mixture was cooled to 0° C. and quenched by the addition of water (0.3 mL), 15% NaOH (0.3 mL) and water (0.9 mL), as described by Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis Vol. 1, Wiley, New York 1967, pp 581-595. The mixture was filtered and the precipitate washed with EtOAc (60 mL). The filtrates were combined and concentrated with toluene to give the crude title compound as a clear oil that was carried forward to the next step without further purification. m/z (APCI+) for C13H18N2O 219.2 (M+H)+.

Workup

  1. customto form a white suspension
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customquenched by the addition of water (0.3 mL), 15% NaOH (0.3 mL) and water (0.9 mL)
  4. customReagents for Organic Synthesis Vol. 1, Wiley, New York 1967, pp 581-595
  5. filtrationThe mixture was filtered
  6. washthe precipitate washed with EtOAc (60 mL)
  7. concentrationconcentrated with toluene

Sources & evidence

ORD record
ord-7691230005a54c81b5be854cc3929e7d
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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