Pyridine → (R)-tert-butyl 1-(hydroxyimino)propan-2-ylcarbamate

HRID 1037967Notes

Reaction equation

HRID 1037967 reaction equation
O=[CH:2][C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].Cl.[NH2:14][OH:15].N1C=CC=CC=1>CO>[OH:15][N:14]=[CH:2][C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 10910049tert-butyl N-((2R)-1-oxopropan-2-yl)carbamate

Product 1

HCID 86657336(R)-tert-butyl 1-(hydroxyimino)propan-2-ylcarbamateYield 157.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (R)-tert-butyl 1-oxopropan-2-ylcarbamate (28.0 g, 81.0 mmol), hydroxylamine hydrochloride (11.2 g, 81.0 mmol), pyridine (60 mL), MeOH (100 mL) was stirred at rt overnight. The solvent was then evaporated. To the residue was added water (100 mL) and the mixture was extracted with DCM (3×200 mL). The combined organic phases were dried (Na2SO4) and concentrated. The crude residue was purified by flash column chromatography (petroleum ether:EtOAc, 4:1) to give (R)-tert-butyl 1-(hydroxyimino)propan-2-ylcarbamate (24.0 g, 79%). 1H NMR (DMSO-d6, 400 MHz) δ 10.63 (s, 1H), 7.20 (d, J=5.2 Hz, 1H), 4.12 (m, 1H), 1.38 (s, 9H), 1.15 (d, J=6.8 Hz, 3H).

Workup

  1. customThe solvent was then evaporated
  2. additionTo the residue was added water (100 mL)
  3. extractionthe mixture was extracted with DCM (3×200 mL)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash column chromatography (petroleum ether:EtOAc, 4:1)

Sources & evidence

ORD record
ord-b3dd9aef91fd4ae6b429b153adccbc80
Source dataset
uspto-grants-2013_10
Patent number
US08546588B2

Reaction notes

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