Reaktion #2303522

Reaktionsgleichung

1,8-diazabicyclo[5.4.0]-7-undecene

2-benzyl-6-pyridyl trifluoromethanesulfonate

(3R,4R)-3,4-dihydroxypyrrolidine acetate

D-tartaric acid

→

title compound

Ausbeute 55.6%

2-Benzyl-6-[(3R,4R)-3,4-dihydroxypyrrolidin-1-yl]pyridine

Ausbeute 55.6%

Lösungsmittel

N-methylpyrrolidone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturby heating
2. 2
   Temperaturto cool
3. 3
   Extraktionthe reaction mixture was extracted with ethyl acetate-water
4. 4
   WaschenThe organic layer was washed with water and brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was purified by silica gel column chromatography (ethyl acetate)

Vorschrift

To a mixture of 11.3 g of 2-benzyl-6-pyridyl trifluoromethanesulfonate, 11.3 g of (3R,4R)-3,4-dihydroxypyrrolidine acetate (synthesized from D-tartaric acid as a starting material, Angew. Chem. Int. Ed. Engl., 23(6), 435, 1984) and 10 ml of N-methylpyrrolidone was added dropwise 11 ml of 1,8-diazabicyclo[5.4.0]-7-undecene under nitrogen atmosphere in an oil bath at 100° C., followed by heating under stirring for 6 hours. After standing to cool, the reaction mixture was extracted with ethyl acetate-water. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate), to give 5.35 g of the title compound.

Quelle