Ammonium formate → HCID 131722691, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ammonium formate (119 mg), 20% Pd(OH)2/C (5 mg) and 4-(4-(2-phenylethyl)-1-ethyl-(1H-pyrazol-5-yl))-1-benzylpiperidine di-TFA salt (from the Step F) in methanol (2 mL) was heated at 60° C. for 1.5 h. The solvent was removed under reduced pressure and the residue was purified by preparative reverse-phase HPLC using a 9.4×250 mm Semi-preparative Zorbax SB-C18 column with 20-35% acetonitrile gradient in water having 0.5% (v/v) TFA over 15 min at 6.25 mL per min to give 4-(4-(2-phenylethyl)-1-ethyl-(1H-pyrazol-5-yl))piperidine di-TFA salt (25 mg) as a gel. 1H NMR (500 MHz, CD3OD): δ7.40 (s, 1 H), 7.22-7.25 (m, 2 H), 7.13-7.17 (m, 3 H), 4.20 (q, J=7.3 Hz, 2 H), 3.42-3.46 (m, 2 H), 3.05-3.15 (m, 3 H), 2.83-2.90 (m, 4 H), 2.04-2.14 (m, 2 H), 1.74-1.79 (m, 2 H), 1.36 (t, J=7.4 Hz, 3 H). The isomer assignment was confirmed by an NOE difference spectrum.

Provenance & Evidence