Downstream synthetic route of (S)-tert-Butyl 2-methylpiperazine-1-carboxylate

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.169447-70-5,(S)-tert-Butyl 2-methylpiperazine-1-carboxylate,as a common compound, the synthetic route is as follows.

^-ieri-Butyl 2-methyl-4-(pyridin-2-yl)piperazine-l-carboxylateTo a solution of ieri-butyl (25)-2-methylpiperazine-l-carboxylate (8 g, 39.94 mmol) in DMSO (25 ml) was added 2-bromopyridine (6.594 g, 41.74 mmol), and DIEA (15.48 g, 119.78 mmol). After stirring 2 days at 120C, the resulting solution was quenched by the addition of DCM (200 ml), washed with water (3 x 300 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a residue, which was purified via silica gel chromatography (3% ethyl acetate in petroleum ether) to afford (S)-tert- butyl 2-methyl-4-(pyridin-2-yl)piperazine-l-carboxylate as a red oil (5.2 g, 47%).LC/MS (ES, m/z): [M+H]+ 278.0’H-NMR (300 MHz, CDC13) delta 8.18 – 8.20 (t, J = 1.8 Hz, 1H), 7.46 – 7.52 (m, 1H), 6.60 – 6.64 (m, 2H), 4.33 – 4.35 (m, 1H), 4.08 – 4.15 (m, 1H), 3.91 – 4.00 (m, 2H), 3.19 – 3.31 (m, 2H), 2.92 – 3.01 (m, 1H), 1.50 (s, 9H), 1.27 – 1.30 (t, / = 4.5 Hz, 3H)

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Reference:
Patent; BIOENERGENIX; MCCALL, John M.; ROMERO, Donna L.; KELLY, Robert C.; WO2012/119046; (2012); A2;,
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