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Description

Covalent Bond’s Cutie Mark Synthesis  
Under a fume hood, chlorinate the oxazole using with chlorine gas, using iron(III) chloride as a catalyst. Fume out the excess chlorine, then purify the 4,5-dichloroxazole (my estimation on the boiling point is ~160-170 C, but I’m just spitballing) Add purified chloroxazole and at least two molar of magnesium metal to THF. This reaction takes a while, so just leave it overnight. Strain out the magnesium, then add two molar of acetaldehyde. Purify out the 4,5-di(2-hydroxyl)ethyloxazole using liquid-liquid extraction; unlike acetaldehyde, chloroxazole, and THF, 4,5-di(2-hydroxyl)ethyloxazole is not water soluble. Hydrogenate the 4,5-di(2-hydroxyl)ethyloxazole to a nickel (or Raney nickel) catalyst in a hydrogen environment at 50C and 60 atm. Next, we need to protect the resulting 4,5-di(2-hydroxyl)ethyloxazolidine from acid catalyzed ring opening; add FMOC chloride to it. Dehydrate the FMOC protected 4,5-di(2-hydroxyl)ethyloxazolidine by refluxing it in 38%(NOT 65%) hydrochloric acid solution. After an hour or so, neutralize any remaining acid by washing the reaction mixture in baking soda solution. Heat the FMOC protected 3,4-diethylideneoxazolidine in formic acid. After another hour, boil off the excess formic acid, then add your FMOC protected 8-hydroxyl-6,9-dimethyl-2,7-dioxa-4-azabicyclo[4.3.0] nonene to a 1:4 mixtrue of tetrachloromethane and DMF. To that, add two molar of triphenylphosphine, then add sodium azide. Heat to 90C and stir. After half an hour, add water to quench the reaction. The FMOC protected 8-amino-6,9-dimethyl-2,7-dioxa-4-azabicyclo[4.3.0] nonene is not water soluble, and should be easy to extract. Deprotect with piperdine then purify with column chromatography. Finally, hydrogenate the deprotected 8-amino-6,9-dimethyl-2,7-dioxa-4-azabicyclo[4.3.0] nonene, as before. This should yield 8-amino-6,9-dimethyl-2,7-dioxa-4-azabicyclo[4.3.0] nonane, the compond represented by Covalent Bond’s cutie mark.

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