3-Azido-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester → Ethyl 3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate

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Reaction Steps

To a solution of 3-azido-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester (1.42 g, 6.28 mmol) in methanol (62 mL) was added Pd (10% weight on carbon, 100 mg). The mixture was degassed and charged with hydrogen (g) 3×, and stirred for 12 hrs. The mixture was filtered through celite and concentrated. The crude residue was purified by flash chromatography (gradient elution: 0→20% MeOH/dichloromethane) to provide 855 mg of a clear oil (68%, 3 steps). 1H NMR (300 MHz, CDCl3) □ ppm 1.26 (t, J=7.1 Hz, 3H), 1.66 (m, 4H), 1.83 (m, 2H), 1.95 (m, 2H), 3.16 (m, 1H), 4.13 (q, J=7.1 Hz, 2H), 4.27 (m, 2H); MS (ESI+Q1MS) m/z 199 [M+H]+

Provenance & Evidence