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

HRID 1946472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1946472
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

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-9e4f903e09dd4b358eb9df5806a75c35
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399444B2

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