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21st August 2013 @ 06:22
Resynthesis of PMY 53-2 for characterisation. Pure SM obtained which should aid synthesis.   AEW 74-1 (330 mg, 1.85 mmol, 1 equiv.) and 10% Pd/C (50 mg, 15 wt%) were suspended in ethanol (12 mL) in EtOH was added to the catalyst suspension and the mixture hydrogenated in the high pressure tube overnight at 100 psi initial. Reaction mixture was stirred for 16.5 hours and the pressure had fallen to 70 psi by morning.  Septum was pierced and the reaction mixture was filtered over Celite, washed with MeOH and evaporated to provide a very pale straw liquid which crystallised at the high vac. 270 mg recovered- indicative of reaction not being complete. Shown by 1H NMR to be a 1:0.8 mixture of product and SM. To be resubmitted to the same reaction conditions at 5pm as hydrogen cylinder in use by UG lab. Stirred for 4 further days at 100psi H2 under the conditions outlined above and then the same work-up was performed. Clear oil with white crystal flakes formed: NMR indicates complete reduction to the desired product with some impurities underneath the aliphatic signals. Decided to use crude in AEW 83-1.   Data: [data]7310[/data][data]7312[/data] [data]7314[/data][data]7316[/data] Hazard and Risk Assessment: [data]7308[/data]
Attached Files
AEW 82-1.png
AEW 82-1 HIRAC.pdf
AEW 82-1 crude 16.5 h.pdf
AEW 82-1.zip
AEW 82-1 4 day proton.pdf
AEW 82-1 4 days.zip