Reaction #6913

Reaction equation

2-iso-Propylsulfonylacetonitrile

Borane dimethylsulfide

HCl

→

title compound

Iso-Propylsulfonylethylamine

Solvents

THF

Conditions

Workup

1. 1
   OtherPrepared
2. 2
   Temperaturewarmed
3. 3
   Temperatureto reflux under N2
4. 4
   Temperatureat reflux
5. 5
   TemperatureAfter cooling
6. 6
   Otherthe reaction to rt
7. 7
   OtherThe volatiles were removed
8. 8
   workup.ADDITIONfrexh methanol was added to the resulting residue
9. 9
   OtherAgain, the volatiles were removed
10. 10
    Washwashed with saturated potassium carbonate (aqueous)
11. 11
    DryingThe organic layer was dried over sodium sulfate
12. 12
    Otherthe volatiles were removed

Procedure

Prepared according to Procedure K. 2-iso-Propylsulfonylacetonitrile (0.50 g, 3.39 mmol) was dissolved in THF and warmed to reflux under N2. Borane dimethylsulfide (2M, 1.7 mL, 3.39 mmol) was added dropwise and the reaction was stirred for an additional 40 minutes at reflux. After cooling the reaction to rt, HCl (2 M in MeOH) was added to the reaction slowly due to gas evolution. The volatiles were removed and frexh methanol was added to the resulting residue. Again, the volatiles were removed and the resulting residue was taken up in CH2Cl2 (25 mL) and washed with saturated potassium carbonate (aqueous). The organic layer was dried over sodium sulfate and the volatiles were removed to afford the title compound. GC-MS m/z 152 (MH+).

Source