Imidazole → N-cyclopentyl-O-tert-butyldimethylsilylhydroxylamine

HRID 857867Notes

Reaction equation

HRID 857867 reaction equation
N1C=CN=[CH:2]1.[C:6]([SiH:10](Cl)[CH3:11])([CH3:9])([CH3:8])[CH3:7].[CH:13]1([NH:18][OH:19])[CH2:17][CH2:16][CH2:15][CH2:14]1>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[CH:13]1([NH:18][O:19][Si:10]([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:11])[CH3:2])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 3

HCID 795ImidazoleHCID 10219393N-cyclopentylhydroxylamineHCID 102463549Tert-butylmethylsilyl chloride

Product 1

HCID 22385752N-cyclopentyl-O-tert-butyldimethylsilylhydroxylamineYield 52.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Imidazole (882 mg) and tert-butylmethylsilyl chloride (903 mg) were added to N-cyclopentylhydroxylamine (650 mg, 6.43 mmol) in dimethylformamide (10 ml). The mixture was stirred at room temperature for 3 hours. After diluting the mixture with ethyl acetate and hexane, the organic layer was washed with water and saturated aqueous sodium chloride. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (hexane-ethyl acetate, 20:1 to 10:1) to give the title compound (722 mg) as a colorless oil.

Workup

  1. washthe organic layer was washed with water and saturated aqueous sodium chloride
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate, 20:1 to 10:1)

Sources & evidence

ORD record
ord-7edb67e9f7664ac4a3c3bfbb906994af
Source dataset
uspto-grants-2006_12
Patent number
US07148224B2

Reaction notes

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