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With palladium on activated charcoal; hydrogen; In methanol; at 20℃; under 760.051 Torr;
To a solution of tert-butyl ((1-benzyl-4-hydroxypiperidin-4-yl)methyl)carbamate (1.3 g, 4.3 mmol) in methanol (20 mL) was added Pd/C (130 mg). The mixture was stirred at room temperature under H2 atmosphere (1 atm) overnight then filtered. The filtrate was concentrated under vacuum to give to give crude tert-butyl methyl(piperidin-3-yl)carbamate as a residue.
With hydrogen;5% rhodium-on-charcoal; In ethanol; at 25℃; under 3102.97 Torr; for 27h;Paar apparatus;
A mixture of tert-butyl 3-pyridinylmethylcarbamate (4.3 g) and 5% rhodium on carbon (400 mg) in ethanol (50 mL) at 25 C. in a paar apparatus was stirred under hydrogen at 60 pounds per square inch for 27 hours, filtered through diatomaceous earth (Celite), and concentrated. 1H NMR (300 MHz, CDCl3) delta 4.55 (b, 1H), 2.99 (m, 4H), 2.56 (t, 1H), 2.33 (t, 1H), 1.74 (m, 1H), 1.66 (m, 2H), 1.44 (s, 9H).
Example 26; N-methyl-N-(piperidin-3-yl) carbamic acid t-butyl ester; [] In a water bath at room temperature, sodium hydride (60% in oil) (0.4 g) was added to a mixture of 3-t-butoxycarbonylaminopiperidin-1-carboxylic acid benzyl ester (compound 25a) (3.3 g), methyl iodide (0.75 mL), and N,N-dimethylformamide (20 mL), and this was stirred at room temperature for four hours. The reaction solution was extracted using ethyl acetate and water, the organic layer was washed with water, and then with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography using 10% to 20% ethyl acetate/ hexane to give an oily substance (3.04 g). A mixture of all of the resulting material with ethanol (20 mL) and 10% palladium on carbon was stirred under hydrogen atmosphere at room temperature for five hours. The catalyst was filtered off, and the filtrate was concentrated to give the title compound (1.82 g).
palladium-carbon; In ethanol; hexane; ethyl acetate; N,N-dimethyl-formamide;
(a) t-Butyl N-methyl-N-(piperidin-3-yl)carbamate 0.4 g of sodium hydride (60%; in oil) was added to a mixture consisting of 3.3 g of benzyl 3-t-butoxycarbonylaminopiperidine-1-carboxylate, 0.75 ml of methyl iodide and 20 ml of N,N-dimethylformamide in a water bath at room temperature. The mixture was stirred at room temperature for 4 hours. The reaction solution was partitioned between ethyl acetate and water, and the organic layer was washed with water and then with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated. The residue was purified by silica gel column chromatography using 10% to 20% ethyl acetate/hexane to give an oily material (3.04 g). This whole ammount was combined with 20 ml of ethanol and 10% palladium carbon. This mixture was stirred at room temperature under a hydrogen atmosphere for five hours. After the catalyst was removed by filtration, the filtrate was concentrated to give 1.82 g of the title compound. 1H-NMR(CDCl3) delta 1.46 (s, 9H) 1.48-1.64 (m, 2H) 1.72-1.84 (m, 2H) 2.43 (dt, J=3 Hz, 12 Hz, 1H) 2.60 (t, J=12 Hz, 1H) 2.75 (s, 3H) 2.74-3.02 (m, 2H) 3.86 (br.s, 1H)
With triethylamine; In tetrahydrofuran; at 20℃; for 16h;
Example 1024tert-buiy methyl(l -(5-nitropyridin-2-yl)piperidin-3-yl)carbamateTo a solution of tert-buty methyl(piperidin-3-yl)carbamate (1 .00 g, 4.67 mmol) in THF (25 mL) was added triethylamine (0.70 mL, 5.0 mmol) and 2-chloro-5-nitropyridine (500 mg, 3.1 mmol). The reaction mixture was then stirred at room temperature for 16 h, diluted with a saturated NaHC03 solution and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated. Purification by column chromatography (silica, ethyl acetate/hexanes) afforded the desired product (1.03 g, 99%) as a yellow solid. ESI MS m/z 337 [Ci6H24 404 + H]+
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