HCID 20336548, compound → HCID 20336539, compound

Participants

Reaction Steps

(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.

Provenance & Evidence