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Stage #1: With hydrogen In methanol at 50℃; Stage #2: With hydrogenchloride In methanol at 20℃; for 2 h;
To a solution of benzyl 4-hydroxybicyclo[2.2.2]octan-l-ylcarbamate (14.8 g, 53 mmol) in methanol (200 mL) was added palladium on charcoal (0.5 g, 10percent). The reaction mixture was stirred at 50 °C under hydrogen atmosphere (50 Psi) overnight and filtered through celite. The filtrate was concentrated and the residue was added to hydrochloric acid in methanol (10percent, 50 mL). The mixture was stirred for 2 h at room temperature. Then the mixture was concentrated again and THF (20 mL) was added. The mixture was stirred at room temperature for 1 h and the precipitate was collected and dried to give the title product (6.7 g, 36 mmol, 70 percent yield).1H NMR (DMSO-< 5) δ 8.00 (s, 3H), 4.48 (br s,lH) ,1.76- 1.80 (m, 6H), 1.58-1.61 (m, 6H). MS (ESI) m/z 142.1 [M+1] +.
methyl 6-chloro-4-((4-hydroxybicyclo[2.2.2]octan-1-yl)amino)nicotinate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With caesium carbonate; at 120℃; for 24h;
To a solution of <strong>[65973-52-6]methyl 4,6-dichloronicotinate</strong> (870 mg, 4.22 mmol) and 1-aminobicyclo[2.2.2]octan-4-ol hydrochloride (500 mg, 2.81 mmol) in butyronitrile (12 mL) was added cesium carbonate (1.98 g, 6.08 mmol). The resulting slurry was heated to 120° C. for 24 hours. The mixture was cooled, diluted with EtOAc, and filtered. The solids were washed with EtOAc and the combined filtrates were concentrated and purified by SiO2 chromotography (eluent: 2-5percent MeOH/CH2Cl2) to provide the desired product. ES/MS: 311.3 (M+H+).
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