Tert-butyl cis-4-azido-3-fluoro-piperidine-1-carboxylate → 1,1-Dimethylethyl (3R,4S)-4-amino-3-fluoro-1-piperidinecarboxylate

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Reaction Steps

Palladium on carbon (10%, 0.876 g, 0.823 mmol) was added to a solution of (cis)-tert-butyl 4-azido-3-fluoropiperidine-1-carboxylate (2.01 g, 8.23 mmol) dissolved in THF and EtOH (1:1, 82 mL). The reaction was placed under a hydrogen atmosphere (balloon pressure) and stirred for 2 hours. The mixture was filtered through GF/F paper and concentrated in vacuo. The amine was purified on a Varian Bond Elut SCX column, eluting with methylene chloride followed by a solution of MeOH containing 6% aqueous NH4OH. The second eluant was concentrated in vacuo to provide the desired product (642 mg). MS ESI (+) m/z 218.8 (M+1) detected.

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