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

HRID 1946474

Reaktionsgleichung

Reaktionsgleichung von HRID 1946474
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][N:12]2[C:16]3[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH2:21][C:15]=3[N:14]=[C:13]2[CH:23]([CH3:25])[CH3:24])[CH:7]=[CH:8][C:9]=1[Cl:10]>ClCCl.CO>[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][N:12]2[C:16]3[CH:17]([OH:22])[CH2:18][CH2:19][CH2:20][CH2:21][C:15]=3[N:14]=[C:13]2[CH:23]([CH3:25])[CH3:24])[CH:7]=[CH:8][C:9]=1[Cl:10]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 584601573-[(3,4-dichlorophenyl)methyl]-2-(1-methylethyl)-5,6,7,8-tetrahydrocyclohepta[d]imidazol-4(3H)-one

Produkt 1

HCID 584601473-[(3,4-Dichlorophenyl)methyl]-2-(1-methylethyl)-3,4,5,6,7,8-hexahydrocyclohepta[d]imidazol-4-olAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Sodium borohydride (204 mg) was added to a stirred solution of Intermediate 7 (630 mg) in dichloromethane (2 mL) and methanol (2 mL). The reaction mixture was stirred for 3 hours. 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 (600 mg). LC/MS MH+ 353/355, Rt 1.13 min (2 minute run).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b5c25d47e394482c9d3a5d4d89a20562
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399444B2

Verknüpfte Notizen

Wird geladen…