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28th February 2013 @ 06:49
Mnr: MNR101-110

Starting material from AEW45-1

Hazard Assement

HIRAC MNR102.pdf


To a mixture of AEW45-1 (75 mg, 0.31 mmol) in methanol (2 mL) under argon was added Pd/C (20 mg).  The flask was then flushed with hydrogen gas three times and left to stir overnight at room temperature.  TLC in the morning showed consumption of starting material but 4 new spots.  The mixture was filtered through celite which was then rinsed with MeOH and concentrated to give the the crude (15 mg).  The celite was then washed with DMF (20 mL) and concentrated at 70 °C / 55 mbar for 2 hours.  Ice was then added to this crude mixture containing some DMF (1-2 mL) and what looked like some solid started to form.  DCM and water was added to the flask and a solid formed at the interface.  This was filered and dried to yeils a pale brown solid (24 mg).

The filtrate was extracted but the organic layer contained mostly DMF.



Unsuccesful reaction.  The NMR of the filtered solid shows many Me peaks and more than one pyrrole H.  There looks to be a solubility problem with this procedure with the SM and product(s). 

Attached Files
HIRAC MNR102.pdf
Re: Reduction of AEW45-1 to give MNR102-1 by OSDD Malaria
26th January 2014 @ 23:05
Note product should be aldehyde, not ketone, in reaction scheme