Triethylamine → tert-Butyl (2S)-2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate

HRID 538734노트

반응식

HRID 538734 반응식
[CH:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=O.C([O-])(=O)C.[NH4+:19].C([N:22](CC)[CH2:23][CH3:24])C>>[NH:19]1[CH:24]=[CH:23][N:22]=[C:1]1[C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

참가 물질

4

반응물 3

HCID 8471TriethylamineHCID 517165Ammonium AcetateHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

생성물 1

HCID 49783269tert-Butyl (2S)-2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate수율 136.9%

반응 조건

온도
140 °C

실험 절차

A mixture of 4 (11.09 g, 25.3 mmol), ammonium acetate (29.25 g, 38.0 mmol) and triethylamine (38.45 g, 38.0 mmol) in xylenes (600 mL) in a sealed tube was stirred at 140° C. for 2 h. After being cooled, the reaction mixture was transferred into a flask and concentrated to dryness. The residue was partitioned between chloroform and H2O, and the organic layer was washed with H2O and concentrated. The crude product was purified by silica gel column chromatography (NH4OH/acetonitrile/ethyl acetate: 1/8/100=(v/v/v)) to afford 5 (8.22 g, 75% yield) as a white solid. LC-MS (ESI): m/z 420.1 (M+H)+.

후처리

  1. temperatureAfter being cooled
  2. customthe reaction mixture was transferred into a flask
  3. concentrationconcentrated to dryness
  4. customThe residue was partitioned between chloroform and H2O
  5. washthe organic layer was washed with H2O
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel column chromatography (NH4OH/acetonitrile/ethyl acetate: 1/8/100=(v/v/v))

출처 및 근거

ORD 기록
ord-c8e851cf96fe452094a34537bcb3aecf
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865756B2

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