With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.129888-60-4,tert-Butyl 3-((methylsulfonyl)oxy)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.
[0373] Step1. A 20 mL vial fitted with a magnetic stir bar was charged with pyrimidine 1(303 mg), mesylate 9 (300 mg) (tert-Butyl3-(methylsulfonyloxy)piperidine-1-carboxylate (9) was prepared according toCosta, et al, J. Med. Chem. 1992, 35, 4334-4343), cesium carbonate (450 mg),and DMF (2 mL). The reaction mixture was heated to 50 C. and stirred for 3 d.The reaction mixture was diluted with water (20 mL) and extracted with EtOAc(3¡Á20 mL). The organic layers were combined, washed with water (3¡Á20 mL) andbrine (1¡Á20 mL). The organic layer was dried over Na2SO4, filtered, andconcentrated under reduced pressure. The resulting residue was redissolved inDCM (3 mL), and treated with TFA (1 mL) and water (0.5 mL). The reactionmixture was stirred for 5 minutes at room temperature and the solutionconcentrated under reduced pressure. The residue was treated with TFA (1 mL)and stirred for 5 minutes and concentrated twice more. The residue was thendiluted with EtOAc and washed with 5% NaHCO3. The organic layer was thenextracted with 1 M HCl. The acid washes were neutralized with NaOH andextracted with EtOAc. The resulting organic layer was dried over Na2SO4,filtered, and concentrated under reduced pressure. The resulting residue wasredissolved in DCM (5 mL) and combined with cyanoacetic acid (170 mg), HOBt(130 mg), DIPEA (0.2 mL), and EDC (250 mg). The reaction mixture was stirredovernight at room temperature. The reaction mixture was diluted with EtOAc,washed with 5% citric acid, followed by 5% NaHCO3, and then brine. The organiclayer dried over Na2SO4, filtered, and concentrated under reduced pressure. Theresulting residue was partially purified by Si-gel chromatography to give3-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperi-din-1-yl)-3-oxopropanenitrile (10) 156 mg (34% yield over 3 steps).
129888-60-4, 129888-60-4 tert-Butyl 3-((methylsulfonyl)oxy)piperidine-1-carboxylate 568122, apiperidines compound, is more and more widely used in various fields.
Reference£º
Patent; Taunton, JR., John William; Brameld, Kenneth Albert; Goldstein, David Michael; Mcfarland, Jesse; Krishnan, Shyam; Choy, Jonathan; US2014/323464; (2014); A1;,
Piperidine – Wikipedia
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