Sodium borohydride → 3-[(4-Chlorophenyl)methyl]-2-(1-methylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-ol

HRID 1946472Notes

Reaction equation

HRID 1946472 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:15]3[C:16](=[O:21])[CH2:17][CH2:18][CH2:19][CH2:20][C:14]=3[N:13]=[C:12]2[CH:22]([CH3:24])[CH3:23])=[CH:6][CH:5]=1>ClCCl.CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][N:11]2[C:15]3[CH:16]([OH:21])[CH2:17][CH2:18][CH2:19][CH2:20][C:14]=3[N:13]=[C:12]2[CH:22]([CH3:24])[CH3:23])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 584602263-[(4-chlorophenyl)methyl]-2-(1-methylethyl)-5,6,7,8-tetrahydrocyclohepta[d]imidazol-4(3H)-one

Product 1

HCID 584602253-[(4-Chlorophenyl)methyl]-2-(1-methylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-olYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (100 mg) was added to a stirred solution of Intermediate 3 (420 mg) in dichloromethane (3 ml) and methanol (3.00 ml). The reaction mixture was stirred for 1 hour. The reaction mixture was partitioned between EtOAc (50 ml) and water (30 ml). The two phases were separated and the aqueous phase was extracted again with EtOAc (30 ml). The phases were separated, the organic extracts were combined, dried (hydrophobic frit) and concentrated under vacuum to give the title compound (376 mg). LC/MS MH+ 319, Rt 0.77 min (2 minute run).

Workup

  1. customThe reaction mixture was partitioned between EtOAc (50 ml) and water (30 ml)
  2. customThe two phases were separated
  3. extractionthe aqueous phase was extracted again with EtOAc (30 ml)
  4. customThe phases were separated
  5. customdried (hydrophobic frit)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9e4f903e09dd4b358eb9df5806a75c35
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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