With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.131685-53-5,(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone,as a common compound, the synthetic route is as follows.
To a solution of S-(+)-4-benzyl-3-propionyl-2-oxazolidinone (100 mg, 429 mumol) in CH2Cl2 (3.0 mL),TiCl4 (60 muL) and N,N,N?N?-tetramethylethylenediamine (160 muL, 1.07 mmol) were added at 0 C under Ar. Cinnamaldehyde (60 muL, 470 mumol) was added and the mixture was stirred at 0 C for 90 min. A saturated NH4Cl aqueous solution (1.0 mL) was added and the suspension was filtered through a Celite pad under suction. After the filtrate was suspended in H2O (15 mL), it was extracted with EtOAc (20 mL ¡Á2).The combined organic solution was washed with brine, dried over MgSO4, and then concentrated in vacuo. Silica gel column chromatography of the residue (EtOAc:hexane = 30:70) gave the aldol adduct (30.0 mg, 85%) as a white, amorphous solid. 1H-NMR (CDCl3) delta 1.26 (3H, d, J = 7.0 Hz), 2.71 (1H, dd, J = 9.5, 13.5Hz), 2.79 (1H, d, J = 7.3 Hz, exchangeable), 3.28 (1H, dd, J = 3.4, 13.5 Hz), 4.15 (1H, dd, J = 3.4, 9.5 Hz), 4.20 (1H, t, J = 9.1 Hz), 4.47 (1H, ddd, 1.0, 7.3, 14.3 Hz), 4.70 (1H, m), 6.29 (1H, dd, J = 7.3, 16.0 Hz), 6.67 (1H, dd, J = 1.0, 16.0 Hz), 7.16-7.41 (10H, aromatic protons). The 1H-NMR spectrum is in accordance with the spectrum reported by Evans.4, 131685-53-5
The synthetic route of 131685-53-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Ito, Atsushi; Kumagai, Ikuya; Maruyama, Miku; Maeda, Hayato; Tonouchi, Akio; Nehira, Tatsuo; Kimura, Ken-Ichi; Hashimoto, Masaru; Tetrahedron Letters; vol. 57; 10; (2016); p. 1117 – 1119;,
Oxazolidine – Wikipedia
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