Lithium aluminum hydride → (2-Amino-1-cyclohexyl-1H-benzimidazol-5-yl)methanol

HRID 2068286Notes

Reaction equation

HRID 2068286 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][C:15]([C:17](OCC)=[O:18])=[CH:16][C:4]=2[N:3]=1.[AlH4-].[Li+]>O1CCCC1>[NH2:1][C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[C:5]2[CH:13]=[CH:14][C:15]([CH2:17][OH:18])=[CH:16][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 67254051Ethyl 2-amino-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylate

Product 1

HCID 67252967(2-Amino-1-cyclohexyl-1H-benzimidazol-5-yl)methanolYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 20 mL vial, ethyl 2-amino-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylate (101.5 mg, 0.0003532 mol) was dissoled in tetrahydrofuran (2 mL, 0.02 mol). While stirring under nitrogen, a solution of 1.0 M of lithium tetrahydroaluminate in tetrahydrofuran (1.0 mL) was added dropwise via a syringe to the reaction mixture. An initial reddish color occured followed by the reaction mixture becoming straw colored and a precipitate formed. After 1 hour the reaction was quenched by the dropwise addition of saturated ammonium chloride (1 mL). The mixture was extracted with ethyl acetate three times, the combined organic phases dried over sodium sulfate and concentrated to give the title compound (79.4 mg) as an off white solid.

Workup

  1. customa precipitate formed
  2. customAfter 1 hour the reaction was quenched by the dropwise addition of saturated ammonium chloride (1 mL)
  3. extractionThe mixture was extracted with ethyl acetate three times
  4. dry with materialthe combined organic phases dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-da6c08cc747247829872a0732a547e8c
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

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