Hydrochloric Acid → 3-Benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione

HRID 1497420Notes

Reaction equation

HRID 1497420 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[CH:13]2[N:16](CC3C=CC=CC=3)[CH:10]([CH2:11][CH2:12]2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO.[Pd]>[CH2:1]([N:8]1[C:9](=[O:24])[CH:10]2[NH:16][CH:13]([CH2:12][CH2:11]2)[C:14]1=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 166374903,8-Dibenzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione

Product 1

HCID 148395753-Benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dioneYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 3,8-dibenzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione (0.00025 mol, 80 mg) in MeOH (2 mL) containing few drops of HCl was hydrogenated with 10% Pd—C (8 mg) for 4 h at room temperature. After completion of the reaction (checked by TLC), the reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, 60-120 mesh; EA-Hexane, 6:4) to afford the 3-benzyl-3,8-diazabicyclo[3.2.1]octane-2,4-dione (LXVI) in 80% yield.

Workup

  1. customAfter completion of the reaction (checked by TLC)
  2. filtrationthe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude residue was purified by column chromatography (silica gel, 60-120 mesh; EA-Hexane, 6:4)

Sources & evidence

ORD record
ord-ff72e006f49446feaee0918af2e179af
Source dataset
uspto-grants-2015_12
Patent number
US09199968B2

Reaction notes

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