Aluminium lithium hydride → HCID 57550203, compound

HRID 1716863Notes

Reaction equation

HRID 1716863 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[N:12]([CH3:32])[C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][N:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[N:25]=[CH:24]3)=[CH:18][CH:17]=2)=[N:14][CH:15]=1)=O>O1CCCC1>[N:23]1([CH2:22][C:19]2[CH:18]=[CH:17][C:16]([C:13]3[N:12]([CH3:32])[C:11]([CH2:9][OH:8])=[CH:15][N:14]=3)=[CH:21][CH:20]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[CH:24]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57550230HCID 57550230, compound

Product 1

HCID 57550203HCID 57550203, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

To a suspension of lithium aluminum hydride (60.8 mg, 1.6 mmol) in anhydrous tetrahydrofuran (4 mL) under nitrogen cooled to −5° C. was added dropwise a solution of 2-(4-benzoimidazol-1-ylmethyl-phenyl)-3-methyl-3H-imidazole-4-carboxylic acid methyl ester (280 mg, 0.8 mmol) in anhydrous tetrahydrofuran (2 mL) over 10 min and the reaction mixture was allowed to stir at for 1 h. The reaction mixture was quenched with water (0.06 mL), aqueous sodium hydroxide (2.5 N, 0.21 mL), and again water (0.06 mL), stirred for 30 min, then diluted with tetrahydrofuran (20 mL) and left overnight without stirring. The reaction mixture was diluted with dichloromethane (20 mL) and methanol (20 mL) and the solid was filtered off. The filtrate was evaporated under reduced pressure and the crude product was used in the next step without further purification. LCMS (ESI+) 319.2 (MH+).

Workup

  1. customThe reaction mixture was quenched with water (0.06 mL), aqueous sodium hydroxide (2.5 N, 0.21 mL), and again water (0.06 mL)
  2. stirringstirred for 30 min
  3. additiondiluted with tetrahydrofuran (20 mL)
  4. waitleft overnight
  5. stirringwithout stirring
  6. additionThe reaction mixture was diluted with dichloromethane (20 mL) and methanol (20 mL)
  7. filtrationthe solid was filtered off
  8. customThe filtrate was evaporated under reduced pressure
  9. customthe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-366afb9738394f2d9e5f747e89fc0e91
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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