With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.148763-41-1,Methyl N-Boc-piperidine-3-carboxylate,as a common compound, the synthetic route is as follows.
Example 1 – Preparation of Intermediate 1 The synthesis of Intermediate 1 followed General Procedure 1 following. Intermediate 1 To a solution of diisopropylamine (6.55 g, 64.7 mmol, 2.1 eq) in cold THF (-780C, 80 mL) was added n-butyllithium (4.04 g, 63.1 mmol, 2.05 eq), and then stirred for 1 hour at 00C. The reaction mixture was then cooled to -780C and to it was then added 1-(tert-butyl)-3-methylpiperidine-1,3-dicarboxylate (7.5 g, 30.8 mmol, 1 eq). The mixture was stirred for 1 hour, and to it was added methyl iodide (13.12 g, 97.4 mmol, 3.0 eq). The reaction mixture was warmed to room temperature overnight. It was monitored by TLC and LC-MS. After completion, the reaction mixture was quenched with ammonium chloride and extracted with ethyl acetate (2 x 150 mL). The combined organic phases were washed with water and brine, then dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography using silica gel (60-120 mesh size), eluting with 5-10% ethyl acetate in n-hexane to give product (Intermediate 1, 4.8 g, yield: 60.5%) m/z 202 [M- 56]+ 1H NMR (400 MHz, CDCl3) delta 3.87 (d, J = 13.3 Hz, 1H), 3.70 (s, 3H), 3.46 (s, 1H), 3.27 (d, J = 5.9 Hz, 1H), 3.15 (d, J = 13.3 Hz, 1H), 2.04 (dd, J = 12.7, 6.2 Hz, 1H), 1.58 (s, 1H), 1.49 (m, 11H), 1.18 (s, 3H) ppm.
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Reference£º
Patent; VERSEON CORPORATION; SHORT, Kevin Michael; ESTIARTE-MARTINEZ, Maria de los Angeles; KITA, David Ben; SHIAU, Timothy Philip; (340 pag.)WO2016/138532; (2016); A1;,
Piperidine – Wikipedia
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