Aluminium lithium hydride → HCID 20813981, compound

HRID 896385Notes

Reaction equation

HRID 896385 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([CH2:14][N:15]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[N:17]([CH:24]([CH3:26])[CH3:25])[C:16]3=[O:27])[N:10]([CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[C:9]=2[CH:8]=[CH:7][CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:2][CH2:3][C:5]1[C:13]2[N:12]=[C:11]([CH2:14][N:15]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[N:17]([CH:24]([CH3:25])[CH3:26])[C:16]3=[O:27])[N:10]([CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 44442493HCID 44442493, compound

Product 1

HCID 20813981HCID 20813981, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (0° C.) solution of 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-4-carboxylic acid methyl ester (2.36 g, 5.44 mmol) in THF (33 mL) was slowly added 1M LiAlH4 in THF (5.46 mL, 5.46 mmol) under nitrogen. The mixture turned bright yellow and was stirred for 10 min at the same temperature. The mixture was quenched with satd. Na/K tartrate (15 mL) and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine and dried with MgSO4. The residue after concentration was purified by flash chromatography (eluent dichloromethane: acetone 4:1, 3:1, 5:2, 2:1) to give 1-[4-Hydroxymethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one (1.21 g, 55%) as a white foam:

Workup

  1. customThe mixture was quenched with satd
  2. extractionNa/K tartrate (15 mL) and extracted with ethyl acetate (2×30 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationThe residue after concentration
  6. customwas purified by flash chromatography (eluent dichloromethane: acetone 4:1, 3:1, 5:2, 2:1)

Sources & evidence

ORD record
ord-c0685ed716134dac88b2a2fe8749953f
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

Loading…