Discovery of 1-Amino-1-cyclopropanecarbonitrile hydrochloride

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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., 127946-77-4

b) (2S,4S)-4-Hydroxy-1-(1-trifluoromethyl-cyclopropanecarbonyl)-pyrrolidine-2 [0151] [0152] To the (2S,4R)-4-methanesulfonyloxy-1-(1-trifluoromethyl-cyclopropanecarbonyl)-pyrrolidine-2-carboxylic acid methyl ester (71.9 g, 200 mmol) were added under stirring and ice-cooling 2.0 M NaOH (120.0 mL, 240.0 mmol) all at once. The ice bath was removed and the white suspension was stirred at room temperature for 1 h. After neutralization by the addition of 2.0 M HCl (20.0 mL, 40.0 mmol; pH 7), 1-aminocyclopropanecarbonitrile hydrochloride (23.7 g 200 mmol) and sodium 2-ethylhexanoate (37.7 g, 220 mmol) were added all at once and the biphasic reaction mixture was stirred at 70 C. for 22 h and then cooled to 35 C. Dichloromethane (100 mL) and NaCl (16 g) were added and stirring was continued until the NaCl was dissolved (15 min). After acidification with 25% HCl (12 mL, pH 1), the reaction mixture was extracted with dichloromethane (3¡Á200 mL) and all three organic layers were washed separately with 5% NaHCO3 (40 mL pH 8). The combined organic layers were dried (Na2SO4), filtered, and evaporated (35-50 C./?5 mbar), affording beige, crystalline residue (88.5 g) which was dissolved in isobutyl acetate (500 mL) at -110 C. Crystallization, which started after seeding and cooling, was completed by stirring at room temperature for 1 h and at -20 C. for 4 h. Filtration and washing with cold isobutyl acetate gave after drying (10 mbar/55 C./4 h) the title product (47.7 g, 72.0%) as an off white, crystalline powder, mp. 156-157 C. [alpha]D20=-68.9 (c 1.0; CHCl3). 1H NMR (CDCl3, 400 MHz) delta 1.15-1.45 (m, 6H), 1.50-1.60 (m, 2H), 2.17-2.29 (m, 2H), 3.72 (dd, J1=11.8 Hz, J2=4.0 Hz, 1H), 3.98 (d, J=11.8 Hz, 1H), 4.40-4.52 (m, 2H), 4.95 (d, J=9.7 Hz, 1H), 7.93 (s, 1H). ESI-MS (m/z) [M+H]+332 (56).

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Reference:
Patent; Hoffmann-La Roche Inc.; Bartels, Bjoern; Bliss, Fritz; Cueni, Philipp; Pfleger, Christophe; Zutter, Ulrich; US2013/123512; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts