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

HRID 1809559Notes

Reaction equation

HRID 1809559 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.Cl.[NH2:17][OH:18].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[OH:18][N:17]=[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 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylate

Product 1

HCID 72698249Tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylateYield 99.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
14 °C

Procedure

A solution of tert-butyl 4-formylpiperidine-1-carboxylate (50.0 g, 234 mmol) in MeOH (200 mL) and water (200 mL) was cooled in an ice-bath and then hydroxylamine hydrochloride (19.5 g, 272 mmol) and sodium carbonate (12.4 g, 117 mmol) were added. The resulting mixture was stirred at 13-15° C. overnight. The solution was concentrated in vacuo to an aqueous suspension, which was extracted with EtOAc. The organic extract was washed with 100 mL brine, dried (MgSO4), filtered, concentrated to provide tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylate (53.1 g, 99.2% yield) as a white crystalline solid.

Workup

  1. concentrationThe solution was concentrated in vacuo to an aqueous suspension, which
  2. extractionwas extracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with 100 mL brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-03f8f3e0c3c3413ea2c130af2b15ebf7
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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