HCID 20243492, compound → HCID 13619047, compound

HRID 482832Notes

Reaction equation

HRID 482832 reaction equation
C([O:8][CH2:9][CH2:10][CH:11]1[NH:14][C:13](=[O:15])[CH:12]1[CH2:16][CH3:17])C1C=CC=CC=1>[Pd].C(O)(=O)C>[CH2:16]([CH:12]1[CH:11]([CH2:10][CH2:9][OH:8])[NH:14][C:13]1=[O:15])[CH3:17]

Participants

4

Reactant 1

HCID 20243492HCID 20243492, compound

Product 1

HCID 13619047HCID 13619047, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A 1-l flask connected to a hydrogenation apparatus and placed on on air driven magnetic stirrer is charged with 4-(2-benzyloxyethyl)-3-ethyl-azetidin-2-one (19.5 g), glacial acetic acid (200 ml) trifluoroacetic acid (9.47 ml) and 10% Palladium on carbon (2.9 g). The mixture is hydrogenated at room temperature and pressure for about 3 hours, then the catalyst is removed by filtration under vacuum, washing with acetic acid. The solvent is evaporated under reduced pressure by heating to 40°-50° C. and the obtained residue is dissolved in methanol (150 ml). Anhydrous potassium carbonate (17.27 g) is added to the resulting solution and the obtained mixture is stirred for 30 minutes. The inorganic salts are removed by filtration and the filtrate is brought to pH 6 by the addition of dilute acetic acid. The residue which is obtained by evaporating the solvent is taken up with water (100 ml) and extracted with toluene (three 50-ml portions). The toluene extracts are washed with a small amount of water and then discarded while the mother liquors plus the aqueous washes are combined, saturated with (NH4)2SO4 (100 g) and extracted with ethyl acetate (five 50-ml portions). The organic extracts are dried over Na2SO4 and evaporated to dryness under vacuum yielding 9.7 g of 3-ethyl-4-(2-hydroxyethyl)-azetidin-2-one as a 6:4 cis/trans mixture.

Workup

  1. customA 1-l flask connected to a hydrogenation apparatus
  2. customis hydrogenated at room temperature
  3. customthe catalyst is removed by filtration under vacuum
  4. washwashing with acetic acid
  5. customThe solvent is evaporated under reduced pressure
  6. temperatureby heating to 40°-50° C.
  7. dissolutionthe obtained residue is dissolved in methanol (150 ml)
  8. additionAnhydrous potassium carbonate (17.27 g) is added to the resulting solution
  9. customThe inorganic salts are removed by filtration
  10. additionthe filtrate is brought to pH 6 by the addition of dilute acetic acid
  11. customThe residue which is obtained
  12. customby evaporating the solvent
  13. extractionextracted with toluene (three 50-ml portions)
  14. washThe toluene extracts are washed with a small amount of water
  15. extractionextracted with ethyl acetate (five 50-ml portions)
  16. dry with materialThe organic extracts are dried over Na2SO4
  17. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-a7ab33a3d1d64211a2e4f40521c3a466
Source dataset
uspto-grants-1986_03
Patent number
US04576746

Reaction notes

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