Pyridine → tert-Butyl 3-(hydroxyimino)pyrrolidine-1-carboxylate

HRID 622450Notes

Reaction equation

HRID 622450 reaction equation
Cl.[NH2:2][OH:3].N1C=CC=CC=1.[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][C:19](=O)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>C(O)C>[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][C:19](=[N:2][OH:3])[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylate

Product 1

HCID 70701179tert-Butyl 3-(hydroxyimino)pyrrolidine-1-carboxylateYield 68.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.87 g of hydroxylamine hydrochloride and 3.3 ml of pyridine were added to a solution of 2.0 g of 1-(t-butoxycarbonyl)-3-pyrrolidone in 9 ml of ethanol, and the mixture was refluxed for 2 hours. The solvent was then distilled off from the reaction mixture, saturated aqueous sodium bicarbonate solution was added to the residue, and it was extracted with chloroform. The chloroform extract was dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was chromatographed on a silica gel column, using a 2/1 mixture of benzene and ethyl acetate as eluent, giving 1.482 g of 1-(t-butoxycarbonyl)-3-hydroxyiminopyrrolidine as a mixture of syn- and anti-isomers.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. distillationThe solvent was then distilled off from the reaction mixture, saturated aqueous sodium bicarbonate solution
  3. additionwas added to the residue, and it
  4. extractionwas extracted with chloroform
  5. extractionThe chloroform extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThe residue was chromatographed on a silica gel column
  9. additiona 2/1 mixture of benzene and ethyl acetate as eluent

Sources & evidence

ORD record
ord-60438bcaa0e94a9e8030343eae2d8238
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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