Trifluoroacetic acid → 1-Methylethyl 4-[({4-[5-(methylsulfonyl)-2-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylate

Participants

Reaction Steps

The title compound (53 mg, 91%) was prepared as an off-white solid from 1,1-dimethylethyl 4-[({4-[5-(methylsulfonyl)-2-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylate (Example 78, 60 mg, 0.13 mmol) and TFA (0.25 mL) in CH2Cl2 (4 mL) then diisopropylethylamine (1.5 ml) and isopropyl chloroformate (1.0M in toluene, 0.16 mL, 0.16 mmol) in a manner similar to Example 74. 1H NMR (400 MHz, CDCl3): δ 9.12 (s, 1H), 8.21 (d, 1H, J=8.3 Hz), 8.04 (d, 2H, J=8.8 Hz), 7.84 (d, 1H, J=8.3 Hz), 7.00 (d, 2H, J=8.6 Hz), 4.92 (septet, 1H, J=6.3 Hz), 4.21 (bs, 2H), 3.88 (d, 2H, J=6.4 Hz), 3.13 (s, 3H), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 433 (M+H).

Provenance & Evidence