Aluminium lithium hydride → (R)-1-((R)-1-(4-Methoxyphenyl)ethyl)-5-oxopyrrolidine-3-carbaldehyde

HRID 2208973Notes

Reaction equation

HRID 2208973 reaction equation
CON(C)[C:4]([C@@H:6]1[CH2:10][C:9](=[O:11])[N:8]([C@@H:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[CH2:7]1)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C@H:12]([N:8]2[C:9](=[O:11])[CH2:10][C@@H:6]([CH:4]=[O:5])[CH2:7]2)[CH3:13])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 117843172(R)-N-methoxy-1-((R)-1-(4-methoxyphenyl)ethyl)-N-methyl-5-oxopyrrolidine-3-carboxamide

Product 1

HCID 117842859(R)-1-((R)-1-(4-Methoxyphenyl)ethyl)-5-oxopyrrolidine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (R)-N-methoxy-1-((R)-1-(4-methoxyphenyl)ethyl)-N-methyl-5-oxopyrrolidine-3-carboxamide 1.02 (260 mg, 0.85 mmol) in THF (6 mL) at 0° C. was added a solution of LAH in THF (1M, 430 μL, 0.43 mmol). The reaction was stirred for 1 hour and quenched by the addition of KHSO4 (sat aq, 15 mL). The mixture was stirred for 5 minutes and Et2O (20 mL) was added. The layers were separated and the aqueous layer was extracted with Et2O (3×20 mL). The combined organics were dried (MgSO4), filtered and concentrated to afford (R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidine-3-carbaldehyde 1.07.

Workup

  1. customquenched by the addition of KHSO4 (sat aq, 15 mL)
  2. stirringThe mixture was stirred for 5 minutes
  3. additionEt2O (20 mL) was added
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with Et2O (3×20 mL)
  6. dry with materialThe combined organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-11e9435988e34bbc82d61d33d53fd3c0
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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