Application of 161117-83-5 ,Some common heterocyclic compound, 161117-83-5, molecular formula is C11H16N2O3, its 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.
A 5000ml reaction vessel was charged with tert-butyl (2-methoxypyridin-3-yl)carbamate (180g, 0.8mol, 1wt) and diethyl ether (2700ml, 15vol). N, N, N, N-tetramethylethylenediamine (360ml, 2vol) was charged at room temperature and the reaction mixture cooled to -78ºC. n-Butyl lithium (2.5M in hexanes, 972ml, 5.4vol) was charged slowly over 2 hours maintaining an internal temperature below -65ºC. After complete addition the reaction mixture was allowed to warm to -15ºC and the temperature maintained at -15ºC for 2 hours. The reaction mixture was re-cooled to -70ºC and ethylene oxide charged (136g, 3.1mol, 0.75wt) over 1 hour, after complete addition the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was cooled to 0-5ºC and quenched by the slow addition of water (1000ml, 5.5vol). The organic layer was separated and the aqueous extracted with ethyl acetate (4x 1000ml, 4x 5.5vol), the combined organics were washed with water (1000ml, 5.5vol) and dried over magnesium sulphate (100g, 0.55wt). After filtration, the organics were concentrated to give the crude material as an orange oil (272g, 1.5wt). The crude material was purified by column chromatography on silica (700g, 3.9wt) with ethyl acetate:heptanes (1:3) as eluent. Concentration of the desired fractions gave the title compound 42 as a pale yellow viscous oil (121.7g, 57%th.).1H NMR (400MHz, DMSO): d 1.41 (s, 9H), 2.71 (t, J=5.5Hz, 2H), 3.58 (m, 2H), 3.85 (s, 3H), 4.72 (m, 1H), 6.91 (d, J=4.9Hz, 1H), 7.84 (m, 1H), 7.94 (m, 1H), 8.18 (br s, 1H).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 161117-83-5, tert-Butyl (2-methoxypyridin-3-yl)carbamate, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Badland, Matthew; Devillers, Ingrid; Durand, Corinne; Fasquelle, Veronique; Gaudillire, Bernard; Jacobelli, Henry; Manage, Ajith C.; Pevet, Isabelle; Puaud, Jocelyne; Shorter, Anthony J.; Wrigglesworth, Roger; Tetrahedron Letters; vol. 52; 41; (2011); p. 5292 – 5296;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem