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

HRID 622450노트

반응식

HRID 622450 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-60438bcaa0e94a9e8030343eae2d8238
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04771046

반응 노트

불러오는 중…