Thioglycolic Acid → HCID 57940603, compound

Participants

Reaction Conditions

Reaction Steps

5-(2,5-difluorophenyl)-1-[(4-nitrophenyl)sulfonyl]-3-phenyl-1,2,3,6-tetrahydropyridine (1-6, 140 mg, 0.31 mmol) was dissolved in DMF (2 mL) and treated sequentially with mercaptoacetic acid (113 mg, 1.2 mmol) and LiOH hydrate (140 mg, 2.4 mmol). The reaction stirred at 25° C. for 2 h until completion. The reaction was then diluted with EtOAc (20 mL), washed with H2O (3×100 mL) and NaCl (sat. aq.). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was purified using reverse-phase column chromatography (5-95% MeOH—H2O w/0.1% TFA) to provide 5-(2,5-difluorophenyl)-3-phenyl-1,2,3,6-tetrahydropyridine (1-7) as a clear oil. 1H NMR (300 MHz, CDCl3) δ 7.25 (m, 5H), 7.00 (m, 2H), 6.95 (m, 1H), 6.17 (s, 1H), 4.03 (br s, 1H), 3.77 (in, 3H), 3.41 (dd, J=12.9, 5.6 Hz, 1H), 2.85 (dd, J=12.7, 7.5 Hz, 1H); MS 272.33 found 272.3 (M+H+) required.

Provenance & Evidence