Water → HCID 24994333, compound

Participants

Reaction Steps

1,1-Dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (0.34 g, 95%) was prepared as a white solid from 6-[4-(methylsulfonyl)phenyl]-3-pyridinol (Example 146, Step 4, 0.20 g, 0.80 mmol), 1,1-dimethylethyl 4-{[(methylsulfonyl)oxy]methyl}-1-piperidinecarboxylate (0.33 g, 1.12 mmol), K2CO3 (0.23 g, 1.60 mmol) in DMF (7 mL) in a manner similar to Example 139, Step 3. The reaction mixture was cooled to ambient temperature, and poured into water (50 mL). The precipitate was collected and washed with water, air dried to give 1,1-dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.40 (bs, 1H), 8.14 (d, 2H, J=7.5 Hz), 8.01 (d, 2H, J=7.3 Hz), 7.80-7.70 (m, 1H), 7.34 (bs, 1H), 4.18 (bs, 2H), 3.91 (d, 2H, J=6.1 Hz), 3.07 (s, 3H), 2.85-2.65 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.45 (s, 9H), 1.40-1.20 (m, 2H); LRMS (ESI), m/z 447 (M+H).

Provenance & Evidence