Reaktion #53481

Reaktionsgleichung

imidazole

1-{(R*)-[4-(chloromethyl)phenyl](4-chlorophenyl)methyl}-3-[(3,5-difluorophenyl)(methylsulfonyl)methylene]azetidine

sodium iodide

→

1-{(R*)-(4-chlorophenyl)[4-(imidazol-1-ylmethyl)phenyl]methyl}-3-[(3,5-difluorophenyl)(methylsulfonyl)methylene]azetidine

Ausbeute 15.3%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter heating for 3 hours
2. 2
   Temperaturunder reflux
3. 3
   Temperaturunder reflux
4. 4
   Sonstigechromatographed on a silica gel column (particle size 0.06-0.200 mm, diameter 1.0 cm, height 20 cm)
5. 5
   Wascheneluting with 120 cm3 of dichloromethane without fractionating
6. 6
   Sonstigewith a dichloromethane and methanol mixture (98/2 and then 96/4 by volume), collecting 4 cm3 fractions
7. 7
   Einengenconcentrated to dryness under reduced pressure (2.7 kPa)

Vorschrift

0.055 g of imidazole is added to solution of 0.24 g of 1-{(R*)-[4-(chloromethyl)phenyl](4-chlorophenyl)methyl}-3-[(3,5-difluorophenyl)(methylsulfonyl)methylene]azetidine, form A isomer, in 5 cm3 of dichloromethane. After heating for 3 hours under reflux, the mixture is supplemented with 5 mg of sodium iodide. After stirring for 20 hours under reflux, the reaction mixture is cooled to 20° C. and then chromatographed on a silica gel column (particle size 0.06-0.200 mm, diameter 1.0 cm, height 20 cm), eluting with 120 cm3 of dichloromethane without fractionating, and then with a dichloromethane and methanol mixture (98/2 and then 96/4 by volume), collecting 4 cm3 fractions. Fractions 12 to 14 are combined and then concentrated to dryness under reduced pressure (2.7 kPa). 0.039 g of 1-{(R*)-(4-chlorophenyl)[4-(imidazol-1-ylmethyl)phenyl]methyl}-3-[(3,5-difluorophenyl)(methylsulfonyl)methylene]azetidine, form A isomer, is obtained in the form of a white foam.

Quelle