Ethanol → Sodium 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate

HRID 2198445Notes

Reaction equation

HRID 2198445 reaction equation
[N:1]12[C:7](=[O:8])[CH2:6][CH:5]1[CH2:4][C:3](=[O:9])[CH:2]2[C:10]([O:12]CC1C=CC=CC=1)=[O:11].C(O)C.O.C([O-])(O)=O.[Na+:28]>O1CCOCC1.[Pd]>[N:1]12[C:7](=[O:8])[CH2:6][CH:5]1[CH2:4][C:3](=[O:9])[CH:2]2[C:10]([O-:12])=[O:11].[Na+:28]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 516892Sodium BicarbonateHCID 12804725Benzyl 3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

Product 1

HCID 23692747Sodium 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Benzyl 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate (25 mg) is hydrogenated at 40 psi for 1 hr in dioxane (2 ml) containing ethanol (0.5 ml), H2O (0.5 ml), NaHCO3 (8.1 mg) and 10% Pd/C (10 mg). The mixture is filtered to remove the catalyst which is washed with more H2O (2.5 ml). The combined filtrate and washing is extracted with EtOAc (3×2 ml), concentrated under reduced pressure, and lyophilized to provide sodium 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate.

Workup

  1. filtrationThe mixture is filtered
  2. customto remove the catalyst which
  3. washis washed with more H2O (2.5 ml)
  4. washThe combined filtrate and washing
  5. extractionis extracted with EtOAc (3×2 ml)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3e0846312c9401ab2f377e447c81629
Source dataset
uspto-grants-1982_11
Patent number
US04357342

Reaction notes

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