Ammonium formate → rac-tert-butyl (3R,4R)-4-amino-3-fluoropiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A stirred solution of trans-4-benzylamino-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester (0.170 g, 0.551 mmol) in methanol (2 ml) and was treated with ammonium formate (0.139 g, 2.20 mmol) and 10% palladium on activated carbon (0.059 g, 0.055 mmol) and stirred at 50° C. for one hour. The mixture was then filtered through Celite, washed with copious methanol and concentrated under vacuum to give 118 mg (100%) of trans-4-amino-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester that was used without further purification. LCMS (Method F): RT=0.14 min, m+H=219.0; 1H NMR (400 MHz, DMSO) δ 4.22-4.01 (m, 1H), 3.96-3.68 (m, 2H), 3.62-3.52 (m, 1H), 3.22-2.94 (m, 2H), 2.89-2.77 (m, 1H), 1.81-1.63 (m, 2H), 1.39 (s, 10H), 1.28-1.16 (m, 1H).

Provenance & Evidence