反应 #46339

反应方程式

sodium borohydride

magnesium sulfate

1-[Bis(4-chlorophenyl)methyl]-3-(phenylsulfonylmethyl)azetidine

sodium borohydride

sodium borohydride

3-(phenylsulfonylmethylene)azetidine

→

3-(phenylsulfonylmethyl)azetidine

溶剂

dichloromethane

water

ethanol

dichloromethane

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture is kept stirring for 20 hours at 20° C
2. 2
   workup.STIRRINGkept stirred for 2 hours and 30 minutes at 50° C.
3. 3
   温度cooled to room temperature
4. 4
   过滤filtered
5. 5
   其他evaporated to dryness under reduced pressure (2.7 kPa)
6. 6
   其他The residue is chromatographed on a silica gel column (particle size 0.063-0.200 mm, height 15 cm, diameter 1 cm)
7. 7
   洗涤eluting under an argon pressure of 0.5 bar
8. 8
   workup.ADDITIONwith a mixture of cyclohexane and ethyl acetate (80/20 by volume)
9. 9
   其他collecting 5-cm3 fractions
10. 10
    浓缩concentrated to dryness under reduced pressure (2.7 kPa)

实验过程

1-[Bis(4-chlorophenyl)methyl]-3-(phenylsulfonylmethyl)azetidine may be prepared by carrying out the procedure in the following manner: 13 mg of sodium borohydride are added, under argon, to a solution of 0.15 g of 1-[bis(4-chlorophenyl)methyl)]-3-(phenylsulfonylmethylene)azetidine in 3 cm3 of anhydrous ethanol and 3.5 cm3 of anhydrous dichloromethane. After stirring for 1 hour and 45 minutes, 14 mg of sodium borohydride are again added and then the mixture is kept stirring for 20 hours at 20° C. The reaction mixture is then heated to 50° C., supplemented with 9.5 mg of sodium borohydride and kept stirred for 2 hours and 30 minutes at 50° C. and then cooled to room temperature. 0.5 cm3 of water, 10 cm3 of dichloromethane and then 50 mg of magnesium sulfate are then added to the mixture, filtered and then evaporated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.063-0.200 mm, height 15 cm, diameter 1 cm), eluting under an argon pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (80/20 by volume) and collecting 5-cm3 fractions. Fractions 12 to 19 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 29 mg of 1-[bis(4-chlorophenyl)methyl)]-3-(phenylsulfonylmethyl)azetidine are obtained in the form of a white solid [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): from 2.75 to 8.90 (mt: 3H); 3.32 (mt: 2H); 3.37 (d, J=7 Hz: 2H); 4.22 (s: 1H); from 7.20 to 7.30 (mt: 8H); 7.57 (broad t, J=7.5 Hz: 2H); 7.67 (tt, J=7.5 and 1.5 Hz 1H); 7.88 (broad d, J=7.5 Hz: 2H)].

来源