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

HRID 1478950Notes

Reaction equation

HRID 1478950 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-f28199fbcb92413bb69d951fa3b88281
Source dataset
uspto-grants-2016_08
Patent number
US09404081B2

Reaction notes

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