4-Piperidinecarboxylic acid, 2-thioxo-, methyl ester synthesis
- Product Name:4-Piperidinecarboxylic acid, 2-thioxo-, methyl ester
- CAS Number:1313498-22-4
- Molecular formula:C7H11NO2S
- Molecular Weight:173.23
25504-47-6
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Yield:1313498-22-4 51%
Reaction Conditions:
with Lawessons reagent in toluene at 100; for 2 h;Inert atmosphere;
Steps:
A Synthesis of methyl 2-thioxopiperidine-4-carboxylate (3):
To a stirred solution of compound 2 (6 g, 38.2 mmol) in toluene (60 mL) was added Lawesson's reagent (7.7 g, 19.1 mmol) under nitrogen atmosphere. The reaction mixture was stirred at 100 °C for 2 h. After consumption of the starting material (by TLC), the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography by eluting with 40% EtOAc/n-hexane to obtain compound 3 (3.4 g, 51 %) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 10.17 (br s, 1H), 3.63 (s, 3H), 3.27-3.21 (m, 2H), 2.95-2.88 (m, 1H), 2.87-2.80 (m, 1H), 2.80-2.72 (m, 1H), 2.05- 1.98 (m, 1H), 1.80-1.70 (m, 1H). LCMS (m/z): 174.1 [M++1].
References:
WO2018/26798,2018,A1 Location in patent:Page/Page column 39; 40
22282-72-0
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24537-50-6
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