cis-4-Benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine → 1,1-Dimethylethyl (3R,4S)-4-amino-3-fluoro-1-piperidinecarboxylate

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Reaction Steps

A mixture of (+/−)-(cis)-tert-butyl-4-(benzylamino)-3-fluoropiperidine-1-carboxylate (100 mg, 0.32 mmol) and 10% Pd/C (10 mg) in methanol (20 mL) was stirred under a balloon of hydrogen for 2 h at room temperature. The reaction mixture was purged with argon, filtered over Celite, rinsed with methanol (10 mL) and the resulting filtrate was concentrated under vacuum to give the title compound as a colorless oil (60 mg, 85%). 1H-NMR (400 MHz, CDCl3) δ ppm: 4.49-4.61 (d, J=48.4 Hz, 1H), 4.30 (s, 1H), 4.07 (s, 1H), 2.84-3.08 (m, 3H), 1.67-1.69 (m, 2H), 1.47 (s, 9H), 1.32 (s, 2H). 19F-NMR (400 MHz in CDCl3): δ ppm: −205.75-206.03 (1F).

Provenance & Evidence