Sodium borohydride → (2,6-Dichloro-3-hydroxymethyl-pyridin-4-yl)-pyrrolidin-1-yl-methanone
Reaktionsgleichung
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[C:4]([Cl:17])[N:3]=1.[BH4-].[Na+]>CCO>[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([C:10]([N:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)=[O:11])[CH:5]=[C:4]([Cl:17])[N:3]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of the above aldehyde and sodium borohydride (400 mg, 10 mmol) in EtOH (50 mL) is stirred at room temperature for 1 hour. After evaporation of EtOH, EtOAc (40 mL) and water (40 mL) are added to the residue. The organic layer is separated, washed once with 1 N NaOH, 1N HCl and brine, dried (Na2SO4) and concentrated. The residue is chromatographed on silica gel (1:1 hexane:EtOAc) to give (2,6-dichloro-3-hydroxymethyl-pyridin-4-yl)-pyrrolidin-1-yl-methanone.