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

HRID 1946523Notes

Reaction equation

HRID 1946523 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[CH:19]([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[CH:19]([CH3:21])[CH3:20])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 584601493-[(4-chlorophenyl)methyl]-2-(1-methylethyl)-3,5,6,7-tetrahydro-4H-benzimidazol-4-one

Product 1

HCID 584601861-[(4-chlorophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-olYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Intermediate 57 (300 mg) in a mixture of methanol (2.5 mL) and dichloromethane (2.5 mL) at ambient temperature was added sodium borohydride (75.0 mg) in one charge. The reaction was stirred at ambient temperature under an atmosphere of nitrogen for 1 hr (incomplete). Stirring continued for 16 hr. The reaction was partitioned between ethyl acetate (40 mL) and water (40 mL). The organic was dried (hydrophobic frit) and concentrated in vacuo to give the title compound (166 mg). LC/MS MH+ 305, 307, Rt 1.38 min (5 min run).

Workup

  1. additioncharge
  2. stirringStirring
  3. waitcontinued for 16 hr
  4. customThe reaction was partitioned between ethyl acetate (40 mL) and water (40 mL)
  5. customThe organic was dried (hydrophobic frit)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8ce6774bd1e431c98e0c74c6ef3135e
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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