HCID 20336548, compound → HCID 20336539, compound

HRID 1706130Notes

Reaction equation

HRID 1706130 reaction equation
[O:1]=[C:2]([CH3:12])/[CH:3]=[C:4]1\[CH2:5][N:6]2[CH:9]([O:10]\1)[CH2:8][C:7]2=[O:11].[H-].C([Al+]CC(C)C)C(C)C>C1C=CC=CC=1.C(OCC)(=O)C.[Cl-].[Na+].O>[OH:1][CH:2]([CH3:12])/[CH:3]=[C:4]1\[CH2:5][N:6]2[CH:9]([O:10]\1)[CH2:8][C:7]2=[O:11]

Participants

6

Reactant 2

HCID 20336548HCID 20336548, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 20336539HCID 20336539, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(E)-3-(2-Oxopropylidene)-4-oxa-1-azabicyclo[3.2.0]heptan-7-one (145 mg., 0.87 mmole) was dissolved in dry benzene (6 ml.) and the solution was stirred and ice-cooled under a dry nitrogen atmosphere while di-iso butyl aluminium hydride (20% solution in toluene, 0.7 ml., 0.98 mmole) was added dropwise. After addition, the mixture was stirred at 0° under dry nitrogen for 4 hours. The mixture was then diluted with ethyl acetate and the solution was shaken with saturated brine. The mixture was filtered, the filtrate was shaken, and the layers were separated. The ethyl acetate layer was dried (magnesium sulphate) and the solvent was evaporated under reduced pressure to give a yellow gum. The gum was chromatographed on silica gel (10 g.) using ethyl acetate/petroleum ether (b.p. 60°-80°) to give the two diastereomers of the title compound. Both isomers were obtained as colourless oils (3 mg. each) and had identical i.r. spectra. νmax (CHCl3): 3500 and 3360 (alcohol OH), 1790 (β-lactam C=O), 1690 (olefinic C=C) cm-1.

Workup

  1. additionwas added dropwise
  2. additionAfter addition
  3. stirringthe mixture was stirred at 0° under dry nitrogen for 4 hours
  4. filtrationThe mixture was filtered
  5. stirringthe filtrate was shaken
  6. customthe layers were separated
  7. dry with materialThe ethyl acetate layer was dried (magnesium sulphate)
  8. customthe solvent was evaporated under reduced pressure
  9. customto give a yellow gum
  10. customThe gum was chromatographed on silica gel (10 g.)

Sources & evidence

ORD record
ord-73bf6f9bf0554976a9a76663275a5067
Source dataset
uspto-grants-1980_06
Patent number
US04206120

Reaction notes

Loading…