Reaktion #638996

Reaktionsgleichung

3-(pyrrolidin-3-yl)pyridine

methyl 1,2,3,4-tetrahydroquinoline-6-carboxylate hydrochloride

diisopropylethylamine

triphosgene

→

methyl 1-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-1,2,3,4-tetrahydroquinoline-6-carboxylate

Ausbeute 176.8%

Lösungsmittel

dichloromethane

Water

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe reaction mixture is left
2. 2
   workup.STIRRINGthe reaction mixture is stirred for eighteen hours
3. 3
   ExtraktionThe aqueous phase is extracted three times with dichloromethane
4. 4
   Waschenwashed with water and with a saturated aqueous sodium chloride solution
5. 5
   Trocknendried over sodium sulfate
6. 6
   Sonstigethe solvent is evaporated under reduced pressure
7. 7
   SonstigeThe residue is chromatographed on silica gel with a dichloromethane/methanol 95/5 mixture

Vorschrift

0.6 g of methyl 1,2,3,4-tetrahydroquinoline-6-carboxylate hydrochloride, 13.2 ml of dichloromethane and 2.54 ml of diisopropylethylamine are placed in a 100 ml round-bottomed flask under a nitrogen atmosphere. 0.31 g of triphosgene is added at 0° C. and then the reaction mixture is left stirring at ambient temperature for three hours. 0.39 g of 3-(pyrrolidin-3-yl)pyridine is subsequently added and the reaction mixture is stirred for eighteen hours. Water and dichloromethane are added. The aqueous phase is extracted three times with dichloromethane. The organic phases are combined, washed with water and with a saturated aqueous sodium chloride solution and dried over sodium sulfate and then the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a dichloromethane/methanol 95/5 mixture. 0.675 g of methyl 1-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-1,2,3,4-tetrahydroquinoline-6-carboxylate is obtained.

Quelle