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

HRID 588506Notes

Reaction equation

HRID 588506 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-d880de63941f4bdaa69283c12c2a1f37
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

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