Methanol → Tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylate

HRID 1972159Notes

Reaction equation

HRID 1972159 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=O.CO.[OH2:18].Cl.[NH2:20]O.C(=O)([O-])[O-].[Na+].[Na+]>>[OH:18][N:20]=[CH:1][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylate

Product 1

HCID 72698249Tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylateYield 98%

Procedure

A mixture of tert-Butyl 4-formylpiperidine-1-carboxylate (30.0 g, 140 mmol), MeOH (150 mL, 3700 mmol) and water (150 mL, 8330 mmol) was cooled in an ice-water bath. Hydroxylamine hydrochloride (11.7 g, 160 mmol) and sodium carbonate (7.45 g, 70 mmol) were added and the resulting mixture was stirred in the ice bath, then allowed to warm to ambient temperature overnight. The reaction was concentrated to an aqueous suspension and was extracted with ethyl acetate. The organic extract was washed with brine, dried, and concentrated to afford the title compound as a white solid (31.3 g, 98%).

Workup

  1. temperaturewas cooled in an ice-water bath
  2. concentrationThe reaction was concentrated to an aqueous suspension
  3. extractionwas extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2ca08b31290d426cb7be9fa1b4465926
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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