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N-(t-butoxycarbonyl)-4-(trifluoromethyl)-4-trimethylsilyloxypiperidine[ No CAS ]
[ 550371-74-9 ]
Yield
Reaction Conditions
Operation in experiment
14%
With methanol; potassium carbonate; at 20℃; for 12.0h;
To a solution of tert-butyl 4-(trifluoromethyl)-4- (trimethylsilyloxy)piperidine-l-carboxylate (0.512 g, 1.50 mmol), in methanol (10 mL) was potassium carbonate (0.25 g, 1.81 mmol). The resulting mixture was stirred at room temperature for 12 hours. Filtration and concentration provided an orange residue that was purified by silica gel chromatography (97:3 dichloromethane:methanol) to give tert-butyl 4-hydroxy-4-(trifluoromethyl)piperidine-l-carboxylate (0.07 g, 14% yield). MS (EI) for CHHI8F3NO3 : 269 (MH+).
14%
With potassium carbonate; In methanol; at 20℃; for 12.0h;
To a solution of tert-butyl 4-(trifluoromethyl)-4-(trimethylsilyloxy)piperidine-l-carboxylate (0.512 g, 1.50 mmol), in methanol (10 mL) was potassium carbonate (0.25 g, 1.81 mmol). The resulting mixture was stirred at room temperature for 12 hours. Filtration and concentration provided an orange residue that was purified by silica gel chromatography (97:3 dichloromethane methanol) to give tert-butyl A- hydroxy-4-(trifluoromethyl)piperidine-l-carboxylate (0.07 g, 14% yield). MS (EI) for
With potassium carbonate; In methanol; at 20℃; for 12.0h;
To a solution of tert-butyl 4-(trifluoromethyl)-4- (trimethylsilyloxy)piperidine-l -carboxylate (0.512 g, 1.50 mmol), in methanol (10 mL) was potassium carbonate (0.25 g, 1.81 mmol). The resulting mixture was stirred at room temperature for 12 hours. Filtration and concentration provided an orange residue that was purified by silica gel chromatography (97:3 dichloromethane:methanol) to give tert-butyl 4- hydroxy-4-(trifluoromethyl)piperidine-l -carboxylate (0.07 g, 14% yield). MS (EI) forC,iH,8F3N03: 269 (MH*).
With trifluoroacetic acid; In dichloromethane; at 20℃; for 0.5h;
To a solution of tert-butyl 4-hydroxy-4-(trifiuoromethyl)piperidine- 1 - carboxylate (0.07 g, 0.26 mmol) in dichloromethane (1 mL) was added trifluoroacetic acid (1 mL). The resulting mixture was stirred at room temperature for 30 minutes. Concentration and drying afforded 4-(trifluoromethyl)piperidin-4-ol (0.044 g, 100%). MS (EI) for C6Hi0F3NO: 269 (MH+).
100%
With trifluoroacetic acid; In dichloromethane; at 20℃; for 0.5h;
To a solution of tert-butyl 4-hydroxy-4-(trifluoromethyl)piperidine-l- carboxylate (0.07 g, 0.26 mmol) in dichloromethane (1 mL) was added trifluoroacetic acid (1 mL). The resulting mixture was stirred at room temperature for 30 minutes. Concentration and drying afforded 4-(trifiuoromethyl)piperidin-4-ol (0.044 g, 100%). MS (EI) for
With trifluoroacetic acid; In dichloromethane; at 25℃; for 12.0h;Inert atmosphere;
Step B: 4-(Trifluoromethyl)piperidin-4-ol Example 5A (1.6g, 5.94mmol) in trifluoroacetic acid (2mL) and dichloromethane (10mL) was reacted at 25C for 12 hours under nitrogen. The reaction mixture was evaporated under reduced pressure to give title compound.
To a solution of tert-butyl 4-hydroxy-4-(trifluoromethyl)piperidine- 1 - carboxylate (0.07 g, 0.26 mmol) in dichloromethane (1 mL) was added trifluoroacetic acid (1 mL). The resulting mixture was stirred at room temperature for 30 minutes. Concentration and drying afforded 4-(trifluoromethyl)piperidin-4-ol (0.044 g, 100%). MS (EI) forC6H,oF3NO: 269 (MH+).
In N,N-dimethyl-formamide; at 0 - 25℃; for 2.0h;Inert atmosphere;
Step A: tert-Butyl 4-hydroxy-4-(trifluoromethyl)piperidine-1-carboxylate To a solution of tert-butyl 4-carbonylhexahydropyridine-1-carboxylate (1.2g, 6.02mmol) in DMF (10mL) was added dropwise trimethyl(trifluoromethyl)silane (3.85g, 27.10mmol) at 0C under nitrogen, and after it was stirred at 25C for 2 hours, quenched by the addition of water (100mL), and the aqueous layer was extracted with ethyl acetate (100mL*3). The combined organic layers were washed with saturated brine (100mL*2), dried over sodium sulfate, filtered and evaporated to give the title compound.
Chemistry
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Material Science
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110K+ Compounds
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