Aluminium lithium hydride → HCID 86679680, compound

HRID 928206Notes

Reaction equation

HRID 928206 reaction equation
[CH2:1]([N:8]1[CH2:12][C@:11]2([O:18][CH3:19])[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([O:18][CH3:19])[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 86679679HCID 86679679, compound

Product 1

HCID 86679680HCID 86679680, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of (+/−)-cis-5-benzyl-3a-methoxytetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione (4.5 g, 17 mmol) in THF (200 mL) was added LAH solution (35 mL, 35 mmol, 1 M in THF) at 0° C. The resulting mixture was stirred at 45° C. overnight. TLC (petroleum ether/EtOAc=1/1) showed the reaction was complete. The mixture was quenched by water (3 mL) and filtered. The filtrate was concentrated to afford crude title compound (3.7 g, crude), which was used for the next step directly.

Workup

  1. customThe mixture was quenched by water (3 mL)
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8b37882bd95141c2969b100a010b42f3
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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