Hydroxylamine → HCID 22991106, compound

HRID 1168110Notes

Reaction equation

HRID 1168110 reaction equation
NO.[Si:3](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)C(C)C)(C)C.Cl.[CH3:31][NH:32][OH:33]>ClCCl.O>[CH3:31][N:32]([Si:3]([C:16]([CH3:19])([CH3:18])[CH3:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:33]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 77906N-methylhydroxylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 22991106HCID 22991106, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

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).

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous layer was extracted with methylene chloride
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe resulting product was purified by liquid chromatography on silica gel using
  7. additiona mixture of hexane and ethyl acetate
  8. washto elute the desired product

Sources & evidence

ORD record
ord-b3151a809b194351870afb540fe21f06
Source dataset
uspto-grants-2003_09
Patent number
US06623721B2

Reaction notes

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