HCID 59598465, compound → HCID 59598488, compound

Participants

Reaction Steps

A solution of (3R)-tert-butyl 3-((2-azidoethoxy)(6-fluoro-3′-methylbiphenyl-2-yl)methyl)piperidine-1-carboxylate (0.89 g) in methanol (20 mL) was added to wetted Pd/C (200 mg). After 3 cycles of evacuation and refilling with H2, a balloon of H2 was attached to the vessel and the mixture was stirred overnight. The reaction mixture was filtered through a pad of Celite and the solvent was removed to give the crude amine. Purification by preparative HPLC gave (3R)-tert-butyl 3-((R)-(2-aminoethoxy)(6-fluoro-3′-methylbiphenyl-2-yl)methyl)piperidine-1-carboxylate (220 mg, 26%). 1H NMR (400 MHz, CDCl3): 1.10 (m, 2H), 1.43 (s, 9H), 1.49 (m, 2H), 1.89 (m, 1H), 2.10 (m, 1H), 2.39 (s, 3H), 3.16 (m, 2H), 3.51 (m, 2H), 4.15 (m, 1H), 6.97 (m, 3H), 7.10 (m, 1H), 7.30-7.48 (m, 3H).

Provenance & Evidence