HCID 22807221, compound → HCID 70568628, compound

HRID 614556Notes

Reaction equation

HRID 614556 reaction equation
[O:1]=[C:2]1[N:8]2[C@H:4]([O:5][C:6]([CH:9]=[CH2:10])=[CH:7]2)[CH2:3]1.[H][H]>O1CCCC1.[Pt]>[CH:9](=[C:6]1[O:5][C@H:4]2[N:8]([C:2](=[O:1])[CH2:3]2)[CH2:7]1)[CH3:10]

Participants

5

Reactant 2

HCID 22807221HCID 22807221, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70568628HCID 70568628, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(5R)-7-oxo-3-vinyl-4-oxa-1-azabicyclo[3.2.0]hept-2-ene (2.4 mmole) in tetrahydrofuran (20 ml) was shaken with 5% platinum on charcoal (150 mg) under 1 atmosphere of hydrogen at room temperature for 1.5 hours. The catalyst was removed by filtration and was washed with tetrahydrofuran. The solvent was evaporated from the filtrate and the residue was chromatographed on silica gel using 1:7 ethyl acetate/petroleum ether (b.p. 60-80°). A mixture of E- and Z- isomers of the title compound was thus obtained as a colourless oil(40 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. washwas washed with tetrahydrofuran
  3. customThe solvent was evaporated from the filtrate
  4. customthe residue was chromatographed on silica gel using 1:7 ethyl acetate/petroleum ether (b.p. 60-80°)
  5. additionA mixture of E- and Z- isomers of the title compound

Sources & evidence

ORD record
ord-09d6853dacce4eba84430dd25c410755
Source dataset
uspto-grants-1979_03
Patent number
US04145430

Reaction notes

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