Sodium Hydroxide → 1,1-Dimethylethyl 4-[({4-[5-(methylsulfonyl)-2-pyridinyl]phenyl}oxy)methyl]-1-piperidinecarboxylate

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Reaction Steps

The title compound (0.20 g, 80%) was prepared as a white solid from 1,1-dimethylethyl 4-({[4-(5-bromo-2-pyridinyl)phenyl]oxy}methyl)-1-piperidinecarboxylate (0.25 g, 0.60 mmol), methanesulfinic acid sodium salt (0.12 g, 80%, 0.91 mmol), L-proline (14 mg, 0.12 mmol), Cul (12 mg, 0.06 mmol) and NaOH (5 mg, 0.12 mmol) in DMSO (3 mL) in a manner similar to Example 76, Step 3. 1H NMR (400 MHz, CD3OD): δ 9.05 (d, 1H, J=2.2 Hz), 8.30 (dd, 1H, Ja=8.4 Hz, Jb=2.3 Hz), 8.09 (d, 2H, J=8.8 Hz), 8.04 (d, 1H, J=8.5 Hz), 7.06 (d, 2H, J=8.8 Hz), 4.20-4.10 (m, 2H), 3.93 (d, 2H, J=6.4 Hz), 3.21 (s, 3H), 2.90-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.46 (s, 9H), 1.35-1.20 (m, 2H); LRMS (ESI), m/z 447 (M+H).

Provenance & Evidence