Sodium Hydroxide → HCID 18187445, compound

Participants

Reaction Steps

1-(t-Butoxycarbonyl)-4-(3,3-difluoro-3-(4-fluorophenyl)propyl)piperidine (122 mg, 0.34 mmol, from EXAMPLE 155, Step G) was dried by evaporation of a toluene solution at reduced pressure. The residue was dissovlved in chloroform (7.6 mL) and iodotrimethylsilane (0.100 mL, 141 mg, 0.70 mmol) was added. After stirring 30 min at RT, the solution was poured into a mixture of saturated aqueous NaHCO3 (15 mL) and 2.5 N NaOH (5 mL), and extracted with ether (50 mL). The organic layer was washed with saturated aq. NaCl (15 ml), dried (Na2SO4), decanted, and evaporated to give the title compound as 88 mg of colorless oil. 1H NMR (500 MHz, CD3OD) δ 7.51 (dd, J=9, 5,22H), 7.17 (t, J=9, 2H), 2.98 (dm, J=12, 2H), 2.52 (td, J=12, 3, 2H), 2.17 (tin, J=16, 2H), 1.65 (bd, J=13, 2H), 1.42-1.26 (m, 3H), 1.07 (qd, J=12, 4, 2H); ESI-MS 258 (M+H); HPLC A: 2.64 min.

Provenance & Evidence