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

HRID 336129ノート

反応式

HRID 336129 の反応式
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

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
215 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-afd1ce3accef4a24a6a29682313a7dae
出典データセット
uspto-grants-2014_11
特許番号
US08889667B2

反応ノート

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