Methanesulfonyl chloride → 1,1-Dimethylethyl 4-[[(methylsulfonyl)oxy]-2-pyridinylmethyl]-1-piperidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-(hydroxy(pyridin-2-yl)methyl)piperidine-1-carboxylate (Prepared in Example 124; 8.00 g, 27.4 mmol) and TEA (11.4 ml, 82.1 mmol) were combined and cooled to 0° C. Methanesulfonyl chloride (2.65 ml, 34.2 mmol) was added and the reaction mixture was stirred at ambient temperature for 18 hours. Water was added and the reaction mixture was extracted with dichloromethane. The organic layer was dried, filtered, and concentrated to give tert-butyl 4-((methylsulfonyloxy)(pyridin-2-yl)methyl)piperidine-1-carboxylate (9.9 g, 97.7% yield). 1H NMR (DMSO-d6) δ 10.88 (bs, 1H), 8.49 (d, 1H), 8.35 (d, 1H), 7.95 (m, 1H), 7.75 (s, 1H), 7.65 (t, 1H), 7.57 (d, 2H), 7.42 (m, 3H), 7.36 (m, 1H), 7.31 (s, 1H), 7.21 (m, 1H), 7.14 (d, 1H), 5.23 (s, 2H), 4.19 (d, 1H), 3.98 (m, 1H), 3.84 (m, 1H), 2.14 (m, 2H), 1.37 (m, 10H), 1.20 (m, 3H), 1.01 (m, 1H).

Provenance & Evidence