Reaktion #413647

Reaktionsgleichung

triethylamine

N-Hydroxysuccinimide

triethylamine

methyl 2-n-butyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-6-carboxylate hydrochloride

benzyloxycarbonyl chloride

→

methyl 2-n-butyl-5-benzyloxycarbonyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-6-carboxylate

Ausbeute 57.5%

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.STIRRINGthe mixture is stirred at room temperature overnight
3. 3
   EinengenThe reaction solution is concentrated under reduced pressure
4. 4
   workup.ADDITIONare added water and chloroform
5. 5
   ExtraktionThe aqueous layer is extracted with chloroform
6. 6
   Sonstigedried
7. 7
   Sonstigeevaporated under reduced pressure
8. 8
   Sonstigeto remove the solvent
9. 9
   SonstigeThe resulting oily residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

Vorschrift

N-Hydroxysuccinimide (0.69 g) and triethylamine (0.6 g) are dissolved in dry dimethylformamide (5 ml), and thereto is added dropwise benzyloxycarbonyl chloride (1.02 g) under ice-cooling. The mixture is stirred for 10 minutes, and thereto is added triethylamine (2.0 g). To the mixture is further added a solution of methyl 2-n-butyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-6-carboxylate hydrochloride (1.55 g) in dimethylformamide (5 ml), and the mixture is stirred at room temperature overnight. The reaction solution is concentrated under reduced pressure, and thereto are added water and chloroform. The aqueous layer is extracted with chloroform, and the extract is combined with the chloroform layer, dried, and evaporated under reduced pressure to remove the solvent. The resulting oily residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give methyl 2-n-butyl-5-benzyloxycarbonyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-6-carboxylate (1.21 g) as pale yellow oil.

Quelle