Some common heterocyclic compound, 18448-47-0, name is Methyl cyclohex-1-enecarboxylate, molecular formula is C8H12O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C8H12O2
Formation of Methyl-1-methylcyclohex-2-ene-1-carboxylate (66a) (2554) To a cold (0 C.) solution of freshly distilled N-isopropylpropan-2-amine (4.20 mL, 29.96 mmol) in THF (150 mL) under argon was added dropwise nBuLi (12.65 mL of 2.2 M solution, 27.82 mmol). After 15 min the solution was cooled to 78 C. and dry HMPA (4.84 mL, 27.82 mmol) was added. The mixture was stirred for 30 min at 78 C. and methyl cyclohexene-1-carboxylate (3.00 g, 21.40 mmol) was then added. After stirring an additional 10 min, methyl iodide (2.00 mL, 32.10 mmol) was added. The solution was then allowed to warm to 5 C. over 2 h. An aqueous saturated solution of NH4Cl was poured into the orange mixture. After dilution with hexanes and washing with brine, the organic layer was dried over Na2SO4 and carefully evaporated to 3.3 g of generate methyl 1-methylcyclohex-2-ene-1-carboxylate, 66a, which was used without further purification. (2555) 1H NMR (300 MHz, CDCl3) delta 5.77 (dt, J=10.1, 3.5 Hz, 1H), 5.66 (s, 1H), 3.71-3.58 (m, 3H), 2.16 (ddd, J=12.9, 7.0, 3.4 Hz, 1H), 2.03-1.88 (m, 2H), 1.72-1.53 (m, 2H), 1.49-1.37 (m, 1H), 1.32-1.14 (m, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18448-47-0, its application will become more common.
Reference:
Patent; Vertex Pharmaceuticals Incorporated; Charifson, Paul S.; Clark, Michael P.; Bandarage, Upul K.; Bethiel, Randy S.; Court, John J.; Deng, Hongbo; Davies, Ioana; Duffy, John P.; Farmer, Luc J.; Gao, Huai; Gu, Wenxin; Jacobs, Dylan H.; Kennedy, Joseph M.; Ledeboer, Mark W.; Ledford, Brian; Maltais, Francois; Perola, Emanuele; Wang, Tiansheng; Wannamaker, M. Woods; Byrn, Randal; Zhou, Yi; Lin, Chao; Jiang, Min; Jones, Steven; Germann, Ursula A.; Salituro, Francesco G.; Kwong, Ann Dak-Yee; (411 pag.)US9345708; (2016); B2;,
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