With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19311-37-6,3-Bromotetrahydrofuran,as a common compound, the synthetic route is as follows.
Step 1: Preparation of Compound 3 (0434) A mixture of tert-butyl N-hydroxy-N-methyl-carbamate (1.00 g, 6.79 mmol, 1.00 eq), 3-bromotetrahydrofuran (1.23 g, 8.15 mmol, 1.20 eq), Cs2CO3 (3.32 g, 10.18 mmol, 1.50 eq) in DMF (10.00 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 70 C. for 16 hour under N2 atmosphere. TLC showed the reaction was completed. The mixture was poured into water (20 mL) and stirred at 5 min. The aqueous phase was extracted with ethyl acetate (15 mL*2). The combined organic phase was washed with brine (20 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by column chromatography (SiO2, Petroleum ether/Ethyl acetate=100/1 to 50/1) to give tert-butyl N-methyl-N-tetrahydrofuran-3-yloxy-carbamate (905.00 mg, 4.17 mmol, 61.35% yield) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 4.62-4.71 (m, 1H) 3.89-4.01 (m, 2H) 3.81-3.88 (m, 1H) 3.75 (dd, J=10.54, 4.39 Hz, 1H) 3.10 (s, 3H) 2.13 (dtdd, J=12.23, 5.32, 5.32, 2.54, 1.32 Hz, 1H) 1.92-2.05 (m, 1H) 1.47-1.53 (m, 9H).
19311-37-6, As the paragraph descriping shows that 19311-37-6 is playing an increasingly important role.
Reference£º
Patent; Novira Therapeutics, Inc.; Hartman, George D.; Kuduk, Scott; (45 pag.)US2016/185777; (2016); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem