Potassium Carbonate → 3-(1-Boc-2-(s)-pyrrolidinylmethoxy)-6-chloro-5-methylpyridine

Beteiligte Stoffe

Reaktionsschritte

To a solution of 5-acetoxy-2-chloro-3-methylpyridine (1.80 g, 8.9 mmol) in MeOH (5 mL) was added potassium carbonate (1.4 g, 10.1 mmol). The reaction mixture was allowed to stir at room temperature for 2.5 h. Solvent was evaporated. The residue was then dissolved in DMF, and 1-BOC-2-(S)-methyltoluenesulfonate-pyrrolidine (2.0 g, 5.63 mmol) from a above was added. The reaction mixture was stirred at 60° C. for 16 h. Solvent was evaporated. The residue was chromatographed (silica gel; hexane/EtOAc, 10:1 to 3:1) to afford an oil (850 mg, 30%): 1H NMR δ 1.47 (s, 9H), 1.80-2.00 (m, 2H), 2.00-2.08 (m, 2H), 2.34 (s, 3H), 3.24-3.44 (m, 2H), 3.92 (m, 1H), 4.02-4.20 (m, 2H), 7.16 (m, 1H), 7.92 (d, 1H, J=2.5 Hz); MS (CI/NH3) m/z 227 (M+H)+.

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