Novel preparation method of lenalidomide
A technology of lenalidomide and glutamine, which is applied in the field of pharmaceutical chemical synthesis, can solve the problems of low total yield, long steps, and difficulty in industrialization, and achieve the effects of low production cost, short reaction steps, and no three wastes
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[0026] Example 1:
[0027] (1) Preparation of 3-N-Boc-aminopiperidine-2,6-dione
[0028] 41.6 g of N-Boc-L-glutamine was dissolved in 200 mL of 2-methyltetrahydrofuran, and 35.1 g of DCC was added under ice bath at 0°C, and reacted at room temperature for 10 hours. Recover the solvent, extract three times with ethyl acetate, combine the organic layers, and use saturated NaHCO 3 , Wash with saturated brine, dry with anhydrous sodium sulfate, recover the solvent to obtain 28.9 g of white solid, the yield is 75%. 1 H NMR (500 MHz, CDCl 3 ) δ: 8.17 (brs, 1H), 5.36 (brs, 1H), 4.33-4.30 (m, 1H), 2.82-2.77 (m, 1H), 2.72-2.64 (m, 1H), 2.54-2.51 (m, 1H), 1.91-1.82 (m, 1H), 1.46 (s, 9H)
Example Embodiment
[0029] Example 2:
[0030] 41.6 g of N-Boc-L-glutamine was dissolved in 200 mL of 2-methyltetrahydrofuran, 35.1 g of DCC was added under an ice bath at 0°C, and reacted at room temperature at 40°C for 10 hours. Recover the solvent, extract three times with ethyl acetate, combine the organic layers, and use saturated NaHCO 3 , Wash with saturated brine, dry with anhydrous sodium sulfate, recover the solvent to obtain a white solid, the yield is 78%.
Example Embodiment
[0031] Example 3:
[0032] (2) Preparation of 3-aminopiperidine-2,6-dione hydrochloride
[0033] 10 g of 3-N-Boc-aminopiperidine-2,6-dione was dissolved in 30 mL of HCl saturated ethyl acetate, stirred at room temperature for 8 hours, and filtered with suction to obtain 6.47 g of white solid with a yield of 90%. 1 H NMR (500 MHz, DMSO-d 6 ): 11.26 (s, 1H), 8.74 (s, 3H), 4.21 (dd, J 1 =13.0 Hz, J 2 = 5.0 Hz, 1H), 2.76-2.68 (m, 1H), 2.61-2.51 (m, 1H), 2.25-2.23 (m, 1H), 2.09-2.00 (m, 1H).
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