HCID 12552183, compound → HCID 12552184, compound

HRID 262161Notes

Reaction equation

HRID 262161 reaction equation
[CH3:1][C:2]1([CH2:7][C:8]([O:10]CC2C=CC=CC=2)=[O:9])[NH:5][C:4](=[O:6])[CH2:3]1>C(O)C.[Pd]>[CH3:1][C:2]1([CH2:7][C:8]([OH:10])=[O:9])[NH:5][C:4](=[O:6])[CH2:3]1

Participants

4

Reactant 1

HCID 12552183HCID 12552183, compound

Product 1

HCID 12552184HCID 12552184, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Methyl 4-benzyloxycarbonylmethyl azetidin-2-one (2) (2.3 g) was dissolved in ethanol (50 ml) and hydrogenated over 10% Pd/C (250 mg) for one hour. The solution was filtered and a further quantity of catalyst (250 mg) added. The hydrogenation was continued for a further hour and the solution filtered through kieselguhr and evaporated. 4-Methyl-4-carboxymethylazetidin-2-one (3) was obtained as a colourless gum which solidified on standing (1.4 g; 98%), νmax (CHCl3 or KBr disc) 3300, 1730, 1695 cm-1. δ ppm (DMSO) 1.38 (3H, s, CH3), 2.57 (2H, s, CH2CO2H), 2.57 and 2.81 (2H, two doublets [AB system] J 14 Hz C3-methylene), 7.90 (1H, s, NH [exchangeable]), 7.0 to 8.5 (1H, br. signal, CO2H [exchangeable]).

Workup

  1. filtrationThe solution was filtered
  2. additiona further quantity of catalyst (250 mg) added
  3. waitThe hydrogenation was continued for a further hour
  4. filtrationthe solution filtered through kieselguhr
  5. customevaporated

Sources & evidence

ORD record
ord-7a0f13e8f0db4ffdb959c21afe7c55bc
Source dataset
uspto-grants-1979_05
Patent number
US04153714

Reaction notes

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