Sodium borohydride → 1-[(3-iodophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-ol
Reaktionsgleichung
[BH4-].[Na+].[I:3][C:4]1[CH:5]=[C:6]([CH2:10][N:11]2[C:15]3[C:16](=[O:20])[CH2:17][CH2:18][CH2:19][C:14]=3[N:13]=[C:12]2[CH:21]([CH3:23])[CH3:22])[CH:7]=[CH:8][CH:9]=1>ClCCl.CO>[I:3][C:4]1[CH:5]=[C:6]([CH2:10][N:11]2[C:15]3[CH:16]([OH:20])[CH2:17][CH2:18][CH2:19][C:14]=3[N:13]=[C:12]2[CH:21]([CH3:23])[CH3:22])[CH:7]=[CH:8][CH:9]=1Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
NaBH4 (1.670 g) was added to a stirred solution of Intermediate 90 (5.8 g) in Dichloromethane (DCM) (30 mL) and Methanol (30 mL). The reaction mixture was stirred at room temperature for 3.5 hours. The reaction mixture was concentrated in vacuo before being partitioned between EtOAc (60 ml) and water (60 ml). The two phases were separated and the aqueous phase was extracted with further EtOAc (2×60 ml). The organic phases were combined, filtered through a hydrophobic frit and concentrated in vacuo to give the desired product (5.7 g) as an off white solid. LC/MS MH+ 397, Rt 2.54 min (5 min run).
Aufarbeitung
- concentrationThe reaction mixture was concentrated in vacuo
- custombefore being partitioned between EtOAc (60 ml) and water (60 ml)
- customThe two phases were separated
- extractionthe aqueous phase was extracted with further EtOAc (2×60 ml)
- filtrationfiltered through a hydrophobic frit
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-0734f925938c4f358f2c2726227e8fcb
- Quelldatensatz
- uspto-grants-2013_03
- Patentnummer
- US08399444B2
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