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

HRID 1946498

Reaktionsgleichung

Reaktionsgleichung von HRID 1946498
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 584602013-[(4-Chlorophenyl)methyl]-2-cyclopropyl-3,4,5,6-tetrahydrocyclopenta[d]imidazol-4-olAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e0b88b8d4939466797f3c091942a60ba
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399444B2

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