Sodium borohydride → 1-[(3-iodophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-ol

HRID 1946549Notes

Reaction equation

HRID 1946549 reaction equation
[BH4-].[Na+].[I:3][C:4]1[CH:5]=[C:6]([CH2:10][N:11]2[C:15]3[C:16](=[O:20])[CH2:17][CH2:18][CH2:19][C:14]=3[N:13]=[C:12]2[CH:21]([CH3:23])[CH3:22])[CH:7]=[CH:8][CH:9]=1>ClCCl.CO>[I:3][C:4]1[CH:5]=[C:6]([CH2:10][N:11]2[C:15]3[CH:16]([OH:20])[CH2:17][CH2:18][CH2:19][C:14]=3[N:13]=[C:12]2[CH:21]([CH3:23])[CH3:22])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 584601523-[(3-iodophenyl)methyl]-2-(1-methylethyl)-3,5,6,7-tetrahydro-4H-benzimidazol-4-one

Product 1

HCID 584601541-[(3-iodophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-olYield 97.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

NaBH4 (1.670 g) was added to a stirred solution of Intermediate 90 (5.8 g) in Dichloromethane (DCM) (30 mL) and Methanol (30 mL). The reaction mixture was stirred at room temperature for 3.5 hours. The reaction mixture was concentrated in vacuo before being partitioned between EtOAc (60 ml) and water (60 ml). The two phases were separated and the aqueous phase was extracted with further EtOAc (2×60 ml). The organic phases were combined, filtered through a hydrophobic frit and concentrated in vacuo to give the desired product (5.7 g) as an off white solid. LC/MS MH+ 397, Rt 2.54 min (5 min run).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custombefore being partitioned between EtOAc (60 ml) and water (60 ml)
  3. customThe two phases were separated
  4. extractionthe aqueous phase was extracted with further EtOAc (2×60 ml)
  5. filtrationfiltered through a hydrophobic frit
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0734f925938c4f358f2c2726227e8fcb
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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