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

HRID 622450ノート

反応式

HRID 622450 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-60438bcaa0e94a9e8030343eae2d8238
出典データセット
uspto-grants-1988_09
特許番号
US04771046

反応ノート

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