Hydroxyamine hydrochloride → Tert-butyl 1-(3-((hydroxyimino)methyl)phenyl)ethylcarbamate

HRID 467505Notes

Reaction equation

HRID 467505 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH:6]=[CH:7][CH:8]=1)=O.C([O-])(=O)C.[Na+].Cl.[NH2:25][OH:26]>C1COCC1>[OH:26][N:25]=[CH:1][C:3]1[CH:4]=[C:5]([CH:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 72407279tert-butyl N-[1-(3-formylphenyl)ethyl]carbamate

Product 1

HCID 76686634Tert-butyl 1-(3-((hydroxyimino)methyl)phenyl)ethylcarbamateYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl N-[1-(3-formylphenyl)ethyl]carbamate (4.0 g, 16.0 mmol) and sodium acetate (3.3 g, 40.1 mmol) in THF (69 mL) at 0° C. was added hydroxylamine hydrochloride (1.4 g, 20.9 mmol). The reaction was allowed to warm to ambient temperature and stirred for 16 hours. The reaction was concentrated in vacuo and the residue partitioned between EtOAc and water and the layers separated. The organic layer was washed with brine (×2), dried (Na2SO4), filtered and concentrated in vacuo to give the sub-title compound as a colourless gel (4.24 g, quantitative Yield). 1H NMR (400 MHz, DMSO) δ 1.30 (d, 3H), 1.33 (d, 9H), 4.61 (dd, 1H), 7.24-7.38 (m, 2H), 7.41 (q, 2H), 7.53 (s, 1H), 8.11 (s, 1H) and 11.20 (s, 1H) ppm; MS (ES+) 265.3.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue partitioned between EtOAc and water
  3. customthe layers separated
  4. washThe organic layer was washed with brine (×2)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d133307ec5564561b23ce34fd453ab9a
Source dataset
uspto-grants-2014_01
Patent number
US08623869B2

Reaction notes

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