Our Policy

Different policies were created to solve this issue, and Carson refused to stop if one step didn’t work.  After using 4 equivalents of LHMDS at-78C in THF and getting extremely low desired yield, Carson is quoted as saying ,“You’d have to be kind of stupid to look at that and not realize that that’s a failure and say we just didn’t do enough of it.”  So he altered his experimental to get higher yield by using catalytic hydrogenation.  


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A solution of 18 (100 mg, 0.163 mmol), formic acid (88%aqueous, 200 microliters), 5% Rh/Al2O3 rhimg (600 mg), MeOH (5 mL) and H2O (15 mL) was maintained under 80 psi of H2 for 12 hours.

The reaction was filtered through a pad of Celite celite (pre-washed with 20 mL of MeOH) and concentrated to give a yellow oil.

This residue was purified by HPLC perf (5 u Alltima reverse phase C18 silica column, 10:14:0.1 Ch3CN-H2O-TFA) to give 44mg(38%) of pure Molecule24 and 34 mg (30%) of an inseparable 10:1 mixture of Molecules 23 and 25, all colorless oils. H-NMR was taken for Molecules 23. Molecules 24 and 25 were byproducts of the hydrogenation reaction.

 

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