Sodium borohydride → 1-[(4-chlorophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-ol

HRID 1946523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1946523
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[C:14](=[O:18])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:19]([CH3:21])[CH3:20])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([OH:18])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:19]([CH3:21])[CH3:20])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 584601493-[(4-chlorophenyl)methyl]-2-(1-methylethyl)-3,5,6,7-tetrahydro-4H-benzimidazol-4-one

Produkt 1

HCID 584601861-[(4-chlorophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-olAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of Intermediate 57 (300 mg) in a mixture of methanol (2.5 mL) and dichloromethane (2.5 mL) at ambient temperature was added sodium borohydride (75.0 mg) in one charge. The reaction was stirred at ambient temperature under an atmosphere of nitrogen for 1 hr (incomplete). Stirring continued for 16 hr. The reaction was partitioned between ethyl acetate (40 mL) and water (40 mL). The organic was dried (hydrophobic frit) and concentrated in vacuo to give the title compound (166 mg). LC/MS MH+ 305, 307, Rt 1.38 min (5 min run).

Aufarbeitung

  1. additioncharge
  2. stirringStirring
  3. waitcontinued for 16 hr
  4. customThe reaction was partitioned between ethyl acetate (40 mL) and water (40 mL)
  5. customThe organic was dried (hydrophobic frit)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d8ce6774bd1e431c98e0c74c6ef3135e
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399444B2

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