(3S,4S)-tert-butyl 4-(benzylamino)-3-fluoropiperidine-1-carboxylate → tert-Butyl (3S,4S)-4-amino-3-fluoropiperidine-1-carboxylate

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Reaction Steps

Pd/C 10% (4.5 g) was added to a solution of (3S,4S) tert-butyl 4-(benzyl amino)-3-fluoropiperidine-1-carboxylate, 2.9 (19.1 g, 0.062 mol) in EtOH (500 mL). The reaction was stirred under hydrogen atmosphere (balloon pressure) for 16 hours at room temperature. After completion of reaction by TLC, the mixture was filtered through celite-bed and concentrated under reduced pressure to obtain the title compound (3S,4S) tert-butyl 4-amino-3-fluoropiperidine-1-carboxylate, 2.11 (12.6 g, 93% yield). 1HNMR (CDCl3, 400 MHz): δ 4.33-4.14 (m, 1H), 4.13-4.02 (m, 2H), 2.94-2.78 (m, 3H), 1.89-1.86 (m, 1H), 1.48 (s, 9H), 1.42-1.34 (m, 1H); LCMS: 100%, m/z 163.1 (M−55, tert-But); HPLC: 99.17%, rt=5.146 min.

Provenance & Evidence