p-Toluenesulfonic acid → HCID 70856308, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of tert-butyl (6-{2-[(1S,2R)-2-(cyanopiperidin-4-yl)cyclopropyl]ethoxy}-5-methylpyridin-3-yl)acetate (650 mg, 1.63 mmol), N-hydroxy-2-methylpropanimidamide (1.38 eq., 230 mg) and zinc chloride (1.58 eq., 350 mg) in 5 mL of DMF was stirred 2 hrs at 80° C., then PTSA (1.0 eq, 280 mg) was added and stirred for additional 2 hrs at 85° C. The mixture was cooled to room temperature and then quenched by said aq soln of NaHCO3. The mixture was extracted with EtOAc (2×75 mL), and the combined organics were then washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by ISCO column (40 g silica gel) using ethyl acetate in hexane (0-40% EA, 400 ml, and 40-100% EA 200 ml) to give the product. LCMS (ESI) m/z 485 [M+H]+.

Provenance & Evidence