Sodium Carbonate → HCID 117849118, compound

Participants

Reaction Conditions

Reaction Steps

A 1,4-dioxane (46 mL)-water (12 mL) solution of tert-butyl (3S,4S)-4-(6-chloropyridin-2-yl)-4-hydroxy-3-(pivaloyloxy)piperidine-1-carboxylate (2.30 g, 5.57 mmol) synthesized in Reference Synthesis Example 152, 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (1.2 mL, 13.4 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium (II) dichloride-dichloromethane complex (915 mg, 1.12 mmol), and sodium carbonate (1.20 g, 11.3 mmol) was stirred under argon atmosphere at 88° C. for 3 hours. After completion of the reaction, saturated ammonium chloride aqueous solution was added to the reaction solution and extraction from the resultant mixture with chloroform was performed. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain the title compound (1.50 g, yield 69%).

Provenance & Evidence