Reaction #1379893

Reaction equation

hydroxylamine

tert-butyldiphenylsilyl chloride

N,N-diisopropylethylamine

N-methyl hydroxylamine hydrochloride

→

N-Methyl,N-(tert-butyldiphenylsilyl)hydroxylamine

Solvents

water

dichloromethane

Conditions

Workup

1. 1
   OtherThe two layers were separated
2. 2
   Extractionthe aqueous layer was extracted with methylene chloride
3. 3
   Dryingdried with magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated to dryness under reduced pressure
6. 6
   OtherThe resulting product was purified by liquid chromatography on silica gel using
7. 7
   workup.ADDITIONa mixture of hexane and ethyl acetate
8. 8
   Washto elute the desired product

Procedure

One possible synthetic scheme for hydroxylamine derivatives involves adding tert-butyldiphenylsilyl chloride and N,N-diisopropylethylamine to a suspension of N-methyl hydroxylamine hydrochloride in dry dichloromethane. The reaction mixture was stirred followed by the addition of water. The two layers were separated and the aqueous layer was extracted with methylene chloride. The organic solutions were then combined, dried with magnesium sulfate, filtered, and concentrated to dryness under reduced pressure. The resulting product was purified by liquid chromatography on silica gel using a mixture of hexane and ethyl acetate to elute the desired product. The purification process gave N-Methyl,N-(tert-butyldiphenylsilyl)hydroxylamine (27).

Source