![271577-10-7](/CAS/GIF/271577-10-7.gif)
1-BOC-4-(2-OXO-3-PYRIDIN-4-YL-PROPYL)-PIPERIDINE synthesis
- Product Name:1-BOC-4-(2-OXO-3-PYRIDIN-4-YL-PROPYL)-PIPERIDINE
- CAS Number:271577-10-7
- Molecular formula:C18H26N2O3
- Molecular Weight:318.41
![4-Methylpyridine](/CAS/GIF/108-89-4.gif)
108-89-4
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$14.00/25mL
![CERIUM(III) CHLORIDE](/CAS/GIF/7790-86-5.gif)
7790-86-5
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$5.00/10g
![Diisopropylamine](/CAS/GIF/108-18-9.gif)
108-18-9
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$10.00/1g
![tert-Butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate](/CAS/GIF/135716-09-5.gif)
135716-09-5
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$9.00/1g
![1-BOC-4-(2-OXO-3-PYRIDIN-4-YL-PROPYL)-PIPERIDINE](/CAS/GIF/271577-10-7.gif)
271577-10-7
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Yield:271577-10-7 25%
Reaction Conditions:
with n-butyllithium;lithium diisopropyl amide in tetrahydrofuran;hexane;
Steps:
A.315.2 Step 2
Step 2 Preparation of 1,1-dimethylethyl 4-[2-oxo-3-(4-pyridinyl)propyl]-1-piperidinecarboxylate To a solution of diisopropylamide (6.15 mL, 43.91 mmol) in dry tetrahydrofuran (40 mL) at 0° C. was added 2.5 M butyl lithium solution in hexane (16.22 mL, 40.53 mmol) dropwise over 10 minutes. After the addition, the lithium diisopropylamide solution was stirred at 0° C. for 20 minutes, then cooled to -78° C. 4-Picoline (3.98 mL, 40.53 mmol) was added to the above lithium diisopropylamide solution under N2 dropwise over 10 minutes. The resulting solution was stirred at -78° C. under N2 for 1.5 hours, then transferred into a suspension of anhydrous cerium chloride (10.0 g, 40.53 mmol) in tetrahydrofuran (40 mL) at -78° C. under N2. The mixture was stirred at -78° C. under N2 for 2 hours, then a solution of ethyl 1-[(1,1-dimethylethoxy)carbonyl]-4-piperidineacetate (from step 1 of this Example) (10.98 g, 40.53 mmol) in tetrahydrofuran (40 mL) was added slowly for 1 hour. The mixture was stirred under N2 from -78° C. to room temperature overnight. The reaction was quenched with water, diluted with ethyl acetate, and washed with a pH 7 buffer. The organic layer was washed with water and brine. After filtration, the solvent was removed under reduced pressure to give a crude product mixture. The desired product 1,1-dimethylethyl 4-[2-oxo-3-(4-pyridinyl)propyl]-1-piperidinecarboxylate (3.19 g, 25%) was isolated by chromatography (silica gel, 50:50-75:25-100:0 ethyl acetate/hexane).
References:
US6423713,2002,B1