[1-(5-BroMo-pyridin-2-yl)-pyrrolidin-3-yl]-carbaMic acid tert-butyl ester synthesis

Yield:1088410-93-8 36%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 100; for 6 h;

Steps:

5

Reference Example 5: Tert-butyl 1-(5-bromopyridin-2-yl)pyrrolidin-3-ylcarbamate 5-Bromo-2-fluoropyridine (1.76 mg, 10 mmol) and 3.62 g (10 mmol) of tert-butyl pyrrolidin-3-ylcarbamate were dissolved in 20 ml of N,N-dimethylformamide. Potassium carbonate (1.38 g, 10 mmol) was added to the solution, and the mixture was stirred at 100°C for 6 hr. Ethyl acetate (60 ml) and 8.5 ml of water were added to the reaction solution, and the organic layer was washed five times with 30 ml of water. The organic layer was dried over anhydrous sodium sulfate and was filtered. The solvent was then removed by distillation, and the residue was purified by column chromatography on silica gel (n-hexane: ethyl acetate = 4: 1) to give 1.23 g (yield 36%) of the title compound. ¹H-NMR (300 MHz, CDCl₃) δ: 1.39 (9H, s),1.5-2.0 (2H, m), 2.6-3.2 (4H, m), 7.05 (1H, d, J = 7.8 Hz), 7.88 (1H, d, J = 7.8 Hz), 8.21 (1H, s) MS (FAB) m/z: 343 (M⁺+1).

References:

EP2166015,2010,A1 Location in patent:Page/Page column 26