The synthetic route of 25504-47-6 has been constantly updated, and we look forward to future research findings.
With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.25504-47-6,Methyl 2-oxopiperidine-4-carboxylate,as a common compound, the synthetic route is as follows.
To a stirred solution of compound 1 (2 g, 12.7 mmol) in THF (15 mL) was added LiHMDS (1.0 M solution in THF, 38.2 mL, 38.2 mmol) slowly at -78 ¡ãC under nitrogen atmosphere. The reaction temperature was raised to -40 ¡ãC and stirred for 1 h. Int-A (3.2 g, 14.0 mmol) in THF (5 mL) was added drop wise at -78 ¡ãC. The reaction mixture was brought to room temperature and stirred for 2 h. After consumption of the starting material (by TLC), the reaction was quenched with aqueous NH4Cl (30 mL) and extracted with CH2CI2 (2 x 100 mL). Organic layer was dried over Na2S04and concentrated under reduced pressure. The crude material was purified by column chromatography by eluting with 5percent MeOH/ CH2CI2 to afford a mixture of AK & AL (2.8 g, 66percent) as brown syrup. Mixture of AK & AL (1 g) was purified by chiral preparative HPLC purification to obtain AK (270 mg) as light brown solid and AL (256 mg) as an off white solid.AK:NMR (400 MHz, DMSO-d6) delta 7.55 (br s, 1H), 6.90 (d, J = 8.5 Hz, 1H), 6.79 (d, J = 8.5 Hz, 1H), 4.32 – 4.16 (m, 2H), 3.78 (d, J = 2.4 Hz, 6H), 3.74 (s, 3H), 3.30 – 3.24 (m, 1H), 3.17 – 3.12 (m, 1H), 3.07 (d, J = 5.6 Hz, 1H), 2.97 (d, J = 5.6 Hz, 1H), 2.34 (s, 2H), 1.98 – 1.77 (m, 2H) LCMS (ESI): m/z 335.2 [M++l]HPLC: 99.71percentChiral HPLC: >99.00percentColumn : CHIRALPAK IC (250*4.6 mm*3qm)Mobile Phase : A: 0.1percent DEA in n-HexaneMobile Phase : B: DCM : MeOH (50 : 50)A : B :: 65 : 35; Plow rate : 1.0 mL/minRetention time : 21.285 minAL:NMR (400 MHz, DMSO-d6) delta 7.55 (br s, 1H), 6.90 (d, J = 8.7 Hz, 1H), 6.79 (d, J = 8.7 Hz, 1H), 4.33 – 4.17 (m, 2H), 3.78 (d, J = 2.6 Hz, 6H), 3.74 (s, 3H), 3.30 – 3.24 (m, 1H), 3.17 – 3.12 (m, 1H), 3.07 (d, J = 5.5 Hz, 1H), 2.97 (d, J = 5.5 Hz, 1H), 2.34 (s, 2H), 1.94 – 1.78 (m, 2H) LCMS (ESI): m/z 335.2 [M++l]HPLC: 99.74percentChiral HPLC: 998.10percentColumn : CHIRALPAK IC (250*4.6 mm* 3 pm)Mobile Phase : A: 0.1percent DEA in n-HexaneMobile Phase : B: DCM : MeOH (50 : 50)A : B :: 65 : 35; Plow rate : 1.0 mL/minRetention time : 24.308 min, 25504-47-6
The synthetic route of 25504-47-6 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; APTINYX INC.; KHAN, M., Amin; (87 pag.)WO2019/152685; (2019); A1;,
Piperidine – Wikipedia
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