1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 8-Boc-3,8-diaza-bicyclo(3.2.1)octane

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Reaction Steps

To a stirred solution of acid VIII (0.00021 mol, 1 eq) in DMF (5 mL), EDCI (0.048 g, 0.00024 mol, 1.1 eq), HOBt (0.038 g, 0.00024 mol, 1.1 eq) and DIPEA (0.15 mL, 0.00078 mol, 2.5 eq) were added at 0° C. and stirred for 15 minutes. A solution of amine LXXI (0.00021 mol, 1 eq) was then added at 0° C. and then the resulting mixture was allowed to stir at room temperature for overnight. After completion of the reaction, water (20 mL) was added and extracted with ethyl acetate (2×30 mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 60-120 mess, 70% ethyl acetate in hexane) to give compound in 49-55% yield.

Provenance & Evidence