Trifluoroacetic acid methylene chloride → HCID 25160186, compound

Participants

Reaction Steps

(±)-tert-Butyl 4-((1-(5-chloro-1-methyl-1H-indazol-7-yl)ethoxy)methyl)-4-phenylpiperidine-1-carboxylate (22 mg, 0.06 mmol) was treated with a trifluoroacetic acid/methylene chloride mixture (1:1, 2 mL) for 1 h. The solvent was removed in vacuo and the resulting crude mixture passed through a strong cation exchange column. After washing the column with several volumes of methanol, the product was eluted by washing the column with 2 M ammonia in methanol. The solvent was evaporated to afford 17 mg (97%) as a clear oil. 1H-NMR (CDCl3, 500 MHz) δ 7.78 (s, 1H), 7.44 (d, J=1.8 Hz, 1H), 7.31-7.37 (m, 4H), 7.20-7.23 (m, 1H), 6.89 (m, 1H), 4.91 (q, J=6.4 Hz, 1H), 4.16 (s, 3H), 3.40 (d, J=9.2 Hz, 1H), 3.35 (d, J=9.2 Hz, 1H), 2.89-2.95 (m, 2H), 2.71-2.79 (m, 2H), 2.12-2.20 (m, 2H), 1.94-2.03 (m, 2H), 1.44 (d, J=6.4 Hz, 3H); 13C-NMR (126 MHz, CDCl3) δ ppm 145.7, 144.3, 135.4, 128.3, 127.8, 127.3, 126.1, 123.2, 122.7, 122.4, 117.1, 78.4, 74.0, 42.8, 42.0, 40.5, 33.4, 22.6. Mass spec.: 384.17 (MH)+.

Provenance & Evidence