With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19099-93-5,1-Cbz-Piperidin-4-one,as a common compound, the synthetic route is as follows.
Step 2: benzyl-7′-chloro-2′-oxo-1′,2′-dihydrospiro[piperidin-4,4′-pyrido[2,3d][1,3]oxazin]-1-carboxylate; Under a nitrogen atmosphere 26.0 mL (173 mmol) N,N,N,N-tetramethylene-ethylenediamine in 180 mL THF were cooled to -20 C. and combined with 70.0 mL (175 mmol) 2.5 M butyllithium solution. After 30 minutes’ stirring the reaction mixture was cooled to -78 C., and at this temperature 17.8 g (78.0 mmol) tert-butyl (6-chloro-pyridin-2-yl)-carbamate in 120 mL THF were slowly added dropwise. The reaction mixture was stirred for 2.5 h at -78 C. and then combined with 27.2 g (117 mmol) Cbz-protected piperidone in 60 mL of THF. After one hour at -78 C. the mixture was heated to RT and then stirred for 18 h at 40 C. The reaction mixture was decomposed by the dropwise addition of 150 mL saturated sodium hydrogen carbonate solution. Then it was extracted with DCM. The combined organic phases were washed with water, dried and evaporated down. The residue was triturated with PE/EtOAc (1/1), the precipitate formed was suction filtered, washed with PE/EtOAc (1/1) and dried.Yield: 16.4 g (54% of theoretical)ESI-MS: m/z=388 (M+H)+ Rt(HPLC): 1.57 min (method B), 19099-93-5
The synthetic route of 19099-93-5 has been constantly updated, and we look forward to future research findings.
Reference：
Patent; Boehringer Ingelheim International GmbH; US2011/172218; (2011); A1;,
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