Dichloromethane → 1-[(4-iodophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-ol

HRID 1946546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1946546
[I: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.ClCCl.[BH4-].[Na+]>CO>[I: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 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 584602073-[(4-iodophenyl)methyl]-2-(1-methylethyl)-3,5,6,7-tetrahydro-4H-benzimidazol-4-one

Produkt 1

HCID 584601671-[(4-iodophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-olAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To Intermediate 87 (6.65 g) in a 250 mL round-bottom flask under nitrogen in Methanol (20 mL) and Dichloromethane (DCM) (20 mL) was added sodium borohydride (1.276 g) in three portions (effervescence) and the mixture stirred at room temperature under nitrogen for 16 h. The solvent was removed under vacuum and the residue was partitioned between ethyl acetate and water. The aqueous layer extracted well with ethyl acetate. The combined organics were dried (hydrophobic frit), filtered and evaporated to give the title compound 6.6 g as a white solid. LC/MS MH+397, Rt 2.61 min (5 min run).

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer extracted well with ethyl acetate
  4. customThe combined organics were dried (hydrophobic frit)
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ec762e1c374c4773b6f4fc2f0cebb631
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399444B2

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