Aluminium lithium hydride → HCID 67197085, compound

HRID 547516Notes

Reaction equation

HRID 547516 reaction equation
C[O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:21])[CH2:12][S:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)=[CH:8][N:7]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([S:13][CH2:12][C:11]([NH:10][CH:9]2[CH2:8][N:7]([CH2:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:6]=[C:5]2[CH2:3][OH:2])=[O:21])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59234712HCID 59234712, compound

Product 1

HCID 67197085HCID 67197085, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

150 mg (0.3 mM) of the compound obtained in Example 1 was dissolved in 2 ml of tetrahydrofuran to which 62 mg (0.9 mM) of lithium aluminum hydride was added dropwise at 0, and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After the reaction was terminated, the resultant was acidified with 1N hydrochloric acid solution, extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure, to obtain 96 mg (68.1%) of the title compound.

Workup

  1. additionwas added dropwise at 0
  2. customAfter the reaction was terminated
  3. extractionextracted with ethyl acetate and brine
  4. dry with materialThe organic solvent layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-6a12f9e0c4944b7e9c390257e5147654
Source dataset
uspto-grants-2011_05
Patent number
US07939550B2

Reaction notes

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