With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.205444-34-4,(S)-tert-Butyl 2-(hydroxymethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.
Boron tribromide (BBr3 12 ml; 1 M in CH2Cl2) was slowly added to a stirred solution of 3-Iodo-5-methoxypyridine (10, 471 mg; 2 mmol) in CH2Cl2 (10 ml) at -40 C (dry ice bath) and reaction mixture was left overnight stirring with gradual warming to ambient temperature. MeOH (7 ml) was slowly added and the reaction mixture was refluxed for 2 h. After removal of solvent, water was added and pH was adjusted to 7-8 by adding Na2CO3. The reaction mixture was extracted with EtOAc, dried over Na2SO4 and concentrated to yield crude product which was purified by prep-TLC using EtOAc/hexanes (1:3) to furnish 3-iodo-5-hydroxypyridine, 11 (300 mg, 68%) as a solid compound. To a solution of 6 (0.20 g, 1.0 mmol), 3-iodo-5-hydroxypyridine (11, 0.24 g, 1.1 mmol) and triphenylphosphine (0.40 g, 1.5 mmol) in THF (10 mL), stirred under argon and cooled at 0 C, was added diisopropyl azodicarboxylate (DIAD; 0.3 mL, 1.5 mmol). The reaction mixture was allowed to come up to ambient temperature over a period of 2 h and was stirred overnight. The reaction mixture was evaporated to dryness and the residue was purified by preparative TLC (30% EtOAc in hexane) to give pure product 12 (0.20 g, 50%) as an oil. 1H NMR (500 MHz, CDCl3) delta ppm: 8.41(d, J = 15.0, 1H, PyH), 8.25 (d, J = 2.0, 1H, PyH), 7.56 (d, J = 18.5, 1H, PyH), 5.88 (m, 2H, olefinic), 4.80 (m, 1H, CH-CH2), 4.34-3.95 (m, 4H, O-CH2, N-CH2), 1.48 (s, 9H, Boc). MS, m/z, 403 (100%, [M+H]+).
205444-34-4, As the paragraph descriping shows that 205444-34-4 is playing an increasingly important role.
Reference£º
Article; Pandey, Suresh K.; Pan, Shawn; Kant, Ritu; Kuruvilla, Sharon A.; Pan, Min-Liang; Mukherjee, Jogeshwar; Bioorganic and Medicinal Chemistry Letters; vol. 22; 24; (2012); p. 7610 – 7614;,
Pyrroline – Wikipedia
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