To a solution of 3-azatricyclo[7.2.1.02,7]dodeca-2,4,6-triene-10,11-diol (Preparation 24, 1.16 g, 6.07 mmol) in ethanol (40 ml) was added sodium periodate (1.35 g, 6.07 mmol) in water (20 ml) to produce a yellow slurry. After 15 min, water and ethyl acetate were added and the layers were separated, the aqueous layer washed with ethyl acetate (4×50 ml) and then dichloromethane. The combined organic extracts were dried (Na2SO4) to give an orange oil. The oil was diluted with dichloroethane (50 ml), benzylamine (0.65 g, 6.07 mmol) was added followed by sodium triacetoxyborohydride (4.12 g, 19.4 mmol). After 7 h, saturated sodium hydrogen carbonate solution (75 ml) and ethyl acetate (75 ml) were added and the reaction mixture was stirred for 20 min. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with water and brine, and then dried (Na2SO4) and concentrated in vacuo to give the crude product. Purification by flash chromatography produced the title compound as a light yellow oil (0.80 g, 50%).
