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

HRID 336129Notes

Reaction equation

HRID 336129 reaction equation
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

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
215 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-afd1ce3accef4a24a6a29682313a7dae
Source dataset
uspto-grants-2014_11
Patent number
US08889667B2

Reaction notes

Loading…