Sodium borohydride → 3-[(4-Chlorophenyl)methyl]-2-cyclopropyl-3,4,5,6-tetrahydrocyclopenta[d]imidazol-4-ol

HRID 1946498Notes

Reaction equation

HRID 1946498 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:19])[CH2:17][CH2:18][C:14]=3[N:13]=[C:12]2[CH:20]2[CH2:22][CH2:21]2)=[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:19])[CH2:17][CH2:18][C:14]=3[N:13]=[C:12]2[CH:20]2[CH2:21][CH2:22]2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 584602283-[(4-chlorophenyl)methyl]-2-cyclopropyl-5,6-dihydrocyclopenta[d]imidazol-4(3H)-one

Product 1

HCID 584602013-[(4-Chlorophenyl)methyl]-2-cyclopropyl-3,4,5,6-tetrahydrocyclopenta[d]imidazol-4-olYield 39.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (94 mg) was added to a stirred solution of Intermediate 29 (238 mg) in dichloromethane (3 ml) and methanol (3.00 ml). The reaction mixture was stirred for 16 hours. The reaction mixture was concentrated under vacuum, partitioned between EtOAc (20 ml) and water (15 ml). The two phases were separated and the aqueous phase was extracted again with EtOAc (2×10 ml). The phases were separated, the organic extracts were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica using a dichloromethane:methanol 0-25% gradient. The fractions were combined and concentrated under vacuum. The residue was purified by MDAP (Method B, UV detection only). The solvent was evaporated in vacuo to give the required product (94 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompartitioned between EtOAc (20 ml) and water (15 ml)
  3. customThe two phases were separated
  4. extractionthe aqueous phase was extracted again with EtOAc (2×10 ml)
  5. customThe phases were separated
  6. customdried (hydrophobic frit)
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified on silica using a dichloromethane
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by MDAP (Method B, UV detection only)
  11. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-e0b88b8d4939466797f3c091942a60ba
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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