Hydrochloric Acid → 8-(4-Hydroxymethyl-bicyclo[2.2.2]oct-1-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

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Reaction Steps

4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester (Example 14) (1.40 g, 3.48 mmol) was combined with LiBH4 (0.379 g, 17.4 mmol), MeOH (0.141 ml, 3.48 mmol), and 100 ml of THF and the resultant mixture was brought to reflux for 18 h. After cooling to rt, 50 ml of 1M HCl were added and the mixture conc'd in vacuo. The residue was dissolved in EtOAc and washed with 1M HCl, sat'd NaHCO3, brine, and dried over Na2SO4. The EtOAc solution was conc'd in vacuo to give 1.15 g (88% yield), of a white solid. (MH+=375.50)

Provenance & Evidence