With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.92235-39-7,(S)-tert-Butyl (2-oxopiperidin-3-yl)carbamate,as a common compound, the synthetic route is as follows.
92235-39-7, A. Preparation of 1,1-dimethylethyl [(3S)-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-2-oxo-3-piperidinyl]carbamate. Lithium bis(trimethylsilyl)amide (1 N in THF, 18.9 mL, 18.9 mmol) in THF (9 mL) was added dropwise over 35 min to a solution of 1,1-dimethylethyl ((3S)-2-oxo-3-piperidinyl)carbamate (2.0 g, 9.3 mmol) in THF (160 mL) stirring at ambient temperature under argon. After stirring at ambient temperature for 15 min the reaction was cooled to 0 C. and a solution of 1-(bromoacetyl)pyrrolidine (2.0 g, 10.4 mmol) in THF (27 mL) was then added over 60 min. After stirring at 0 C. for 2 h, the reaction was quenched with 10% KHSO4 and transferred to a separatory funnel with ethyl acetate. The mixture was washed with 10% KHSO4 and brine, dried over magnesium sulfate and concentrated in vacuo to afford 4.0 g of crude product. Column chromatography (silica, acetonitrile) afforded 1,1-dimethylethyl [(3S)-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-2-oxo-3-piperidinyl]carbamate (2.0 g, 66%): 1H-NMR (CDCl3) delta 5.36 (m, 1H), 4.14 (d, J=14.1 Hz, 1H), 4.00 (m, 1 H), 3.71 (d, J=14.1 Hz, 1 H), 3.41-3.24 (m, 6 H), 2.31 (m, 1 H), 1.91-1.70 (m, 6 H), 1.61 (m, 1 H), 1.42 (s, 9 H); 13C-NMR (CDCl3) delta 170.0, 165.6, 155.6, 79.0, 51.5, 49.3, 48.6, 45.6, 45.5, 28.1, 27.6, 25.9, 23.8, 20.6.
The synthetic route of 92235-39-7 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; Stein, Philip D.; O’Connor, Stephen P.; Shi, Yan; Li, Chi; US2002/25957; (2002); A1;,
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