Triphenylphosphine → N-{1-[bis(4-chloro-phenyl)methyl]azetidin-3-yl}-N-(6-chloropyrid-2-yl)-methylsulfonamide

Participants

Reaction Conditions

Reaction Steps

N-{1-[Bis-(4-chlorophenyl)methyl]azetidin-3-yl}-N-(6-chloropyrid-2-yl)methylsulfonamide may be prepared by carrying out the procedure in the following manner: 2.4 cm3 of diethyl azodicarboxylate and 1.44 g of triphenylphosphine are added, under argon, to a solution of 1.54 g of 1-[bis(4-chlorophenyl)methyl]-azetidin-3-ol and 1.22 g of N-(6-chloropyrid-2-yl)methylsulfonamide in 120 cm3 of anhydrous tetrahydrofuran. After stirring for 20 hours at 20° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.040-0.063 mm, height 30 cm, diameter 4.5 cm), eluting under an argon pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (80/20 by volume) and collecting 60-cm3 fractions. Fractions 6 to 9 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 1.75 g of N-{1-[bis(4-chloro-phenyl)methyl]azetidin-3-yl}-N-(6-chloropyrid-2-yl)-methylsulfonamide are obtained in the form of a white foam [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): from 2.85 to 3.00 (mt: 2H); 2.91 (s: 3H); 3.57 (split t, J=7 and 2 Hz: 2H); 4.25 (s: 1H); 4.64 (mt: 1H); from 7.20 to 7.35 (mt: 9H); 7.36 (dd, J=8 and 1 Hz: 1H); 7.71 (t, J=8 Hz: 1H)].

Provenance & Evidence