Aluminium lithium hydride → HCID 68874198, compound

HRID 1817861Notes

Reaction equation

HRID 1817861 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][C:18]([C:20](OC)=[O:21])=[CH:19][C:14]=3[N:13]=[C:12]2[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:9][CH2:8]1>O1CCCC1>[CH:7]1([CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][C:18]([CH2:20][OH:21])=[CH:19][C:14]=3[N:13]=[C:12]2[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68873538HCID 68873538, compound

Product 1

HCID 68874198HCID 68874198, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of lithium aluminum hydride (391 mg, 8.3 mmol) in tetrahydrofuran (15 mL) was added a tetrahydrofuran solution of methyl 1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazole-5-carboxylate (Step C, 990 mg, 3.3 mmol) at 0° C. The mixture was stirred at 0° C. for 3 h. The mixture was quenched with potassium fluoride and sodium sulfate decahydrate and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2 as eluent) to afford the title compound (573 mg, 64%) as red gum.

Workup

  1. customThe mixture was quenched with potassium fluoride and sodium sulfate decahydrate
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2 as eluent)

Sources & evidence

ORD record
ord-c0d6f1cab7774177a02d5c6dc959fe4c
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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