Sodium Carbonate → tert-Butyl 4-(hydroxyimino)piperidine-1-carboxylate

HRID 1421496Notes

Reaction equation

HRID 1421496 reaction equation
Cl.[NH2:2][OH:3].C([O-])([O-])=O.[Na+].[Na+].[CH3:10][C:11]([O:14][C:15]([N:17]1[CH2:23][CH2:22][C:20](=O)[CH2:19][CH2:18]1)=[O:16])([CH3:13])[CH3:12]>CO>[C:11]([O:14][C:15]([N:17]1[CH2:23][CH2:22][C:20](=[N:2][OH:3])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:10]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 15462924tert-Butyl 4-(hydroxyimino)piperidine-1-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of hydroxylamine hydrochloride (0.84 g, 12.0 mmol) in methanol (10 mL) at 0° C. was added solid Na2CO3 (0.64 g, 6.0 mmol). The mixture was stirred for ca. 5 min. N-t-Boc-4-piperidone (1.99 g, 10.0 mmol) was added and the mixture was stirred for ca 2 h. The reaction mixture was concentrated in vacuo to ca. half its original volume, then diluted with saturated NaHCO3 (100 mL) and extracted with CHCl3 (4×50 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to yield 1.86 g (87%) of the desired product as a tan solid. MS (ES+) m/z 215.0 [M+H]+.

Workup

  1. stirringthe mixture was stirred for ca 2 h
  2. concentrationThe reaction mixture was concentrated in vacuo to ca. half its original volume
  3. additiondiluted with saturated NaHCO3 (100 mL)
  4. extractionextracted with CHCl3 (4×50 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da5281663e9848c48c17fd6d0794b4c6
Source dataset
uspto-grants-2000_06
Patent number
US06077857

Reaction notes

Loading…