2,4-Octanedione → 3,8-Dibenzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione

HRID 336129노트

반응식

HRID 336129 반응식
CC(=O)CC(=O)CCCC.[CH2:11]([N:18]1[CH:22]([C:23](=[O:32])[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:21][CH2:20][CH:19]1[C:33](OCC)=[O:34])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:25]([N:24]1[C:33](=[O:34])[CH:19]2[N:18]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:22]([CH2:21][CH2:20]2)[C:23]1=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

3

반응물 2

HCID 841922,4-OctanedioneHCID 59813968Ethyl 1-benzyl-5-(benzylcarbamoyl)pyrrolidine-2-carboxylate

생성물 1

HCID 166374903,8-Dibenzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione수율 40%

반응 조건

온도
215 °C

실험 절차

2.1]octane-2,4-dione (LXVI). Ethyl 1-benzyl-5-(benzylcarbamoyl)pyrrolidine-2-carboxylate (LXV, 0.00122 mol, 450 mg) was heated under stirring at 210-220° C. for 3 h under atmospheric pressure and the formed ethyl alcohol was collected. After completion of the reaction (checked by TLC), the reaction mixture was cooled at room temperature and the residue was purified by column chromatography (silica gel, 60-120 mesh; EA-Hexane, 2:8) to afford the 3,8-dibenzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione in 40-45% yield.

후처리

  1. customthe formed ethyl alcohol was collected
  2. customAfter completion of the reaction (checked by TLC)
  3. temperaturethe reaction mixture was cooled at room temperature
  4. customthe residue was purified by column chromatography (silica gel, 60-120 mesh; EA-Hexane, 2:8)

출처 및 근거

ORD 기록
ord-afd1ce3accef4a24a6a29682313a7dae
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889667B2

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