Application of 149990-27-2,Some common heterocyclic compound, 149990-27-2, name is tert-Butyl but-3-yn-1-ylcarbamate, molecular formula is C9H15NO2, 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.
Ethyl 2-isocyanoacetate (4.30 mL, 39.34 mmol) was added slowly to tert-butyl but-3-yn-1-ylcarbamate (9.99 g, 59.01 mmol) and Silver carbonate (1.085 g, 3.93 mmol) in 1,4-dioxane (18 mL) at 80C over a period of 10 minutes under nitrogen. The resulting solution was stirred at 80 C for hours. A LCMS indicated the presence of the desired material and also the by-product 6. The reaction mixture was concentrated, dissolved in DCM and filtered. The reaction was purified by flash silica chromatography, elution gradient 0 to 25% EtOAc in heptane. Pure fractions were evaporated to dryness to afford ethyl 3-(2-((tert-butoxycarbonyl)amino)ethyl)-1H-pyrrole-2-carboxylate (5.51 g, 49.6 %) as a colourless oil; MS (ES-) m/z: 281 (M-H)-.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl but-3-yn-1-ylcarbamate, its application will become more common.
Reference:
Article; Greenwood, Ryan; Yeung, Kay; Tetrahedron Letters; vol. 57; 51; (2016); p. 5812 – 5814;,
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