Sodium borohydride → 1-[(4-chlorophenyl)methyl]-2-(1,1-dimethylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-ol

HRID 1946517Notes

Reaction equation

HRID 1946517 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[C:14](=[O:18])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([OH:18])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 584602033-[(4-chlorophenyl)methyl]-2-(1,1-dimethylethyl)-3,5,6,7-tetrahydro-4H-benzimidazol-4-one

Product 1

HCID 584601821-[(4-chlorophenyl)methyl]-2-(1,1-dimethylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-olYield 70.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Intermediate 53 (120 mg) in a mixture of methanol (1.5 mL) and dichloromethane (1.5 mL) at ambient temperature was added sodium borohydride (30 mg) in one charge. The reaction was stirred at ambient temperature under an atmosphere of nitrogen for 2 hr. The reaction was partitioned between ethyl acetate (20 mL) and water (20 mL). The organics were dried (hydrophobic frit) and concentrated in vacuo to give the title compound (85 mg). LC/MS MH+ 319, Rt 1.92 min (5 min run).

Workup

  1. additioncharge
  2. customThe reaction was partitioned between ethyl acetate (20 mL) and water (20 mL)
  3. customThe organics were dried (hydrophobic frit)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ee27b776ef242d18615aa56515c5214
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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