A common compound: 591769-05-0, name is 3-Cyclopentylacrylonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 591769-05-0
To a solution of -4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine (15.0 g,0.0476 mol) in ACN (300 mL) was added 3-cyclopentylacrylonitrile (15 g, 0.12 mol) (as a mixture of cis and trans isomers),followed by DBU (15 mL, 0.10 mol). The resulting mixture was stirred at room temperature overnight. The ACN wasevaporated. The mixture was diluted with ethyl acetate, and the solution was washed with 1.0 N HCl. The aqueous layerwas back-extracted with three portions of ethyl acetate. The combined organic extracts were washed with brine, driedover sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (gradientof ethyl acetate/hexanes) to yield a viscous clear syrup, which was dissolved in ethanol and evaporated several timesto remove ethyl acetate, to afford 19.4 g of racemic adduct (93percent). The enantiomers were separated by preparative-HPLC, (OD-H, 15percent ethanol/hexanes) and used separately in the next step to generate their corresponding final product.The final products (see Step 3) stemming from each of the separated enantiomers were found to be active JAK inhibitors;however, the final product stemming from the second peak to elute from the preparative-HPLC was more active thanits enantiomer.1H NMR (300 MHz, CDCl3): delta 8.85 (s, 1H), 8.32 (s, 2H), 7.39 (d, 1H), 6.80 (d, 1H), 5.68 (s, 2H), 4.26 (dt, 1H),3.54 (t, 2H), 3.14 (dd, 1H), 2.95 (dd, 1H), 2.67-2.50 (m, 1H), 2.03-1.88 (m, 1H), 1.80-1.15 (m, 7H), 0.92 (t, 2H), -0.06(s, 9H); MS(ES):437 (M+1).
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, 591769-05-0, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; Incyte Holdings Corporation; PARIKH, Bhavnish; SHAH, Bhavesh; YELESWARAM, Krishnaswamy; (55 pag.)EP2574168; (2016); B1;,
Nitrile – Wikipedia,
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