Acetone → 2-Methyl-2-(2-methyl-1-pyrrolidinyl)propanenitrile

참여 물질

반응 단계

To a stirred, ice-cooled mixture of 2-(RS)-methylpyrrolidine (4.25 g; 0.05 mol) and acetone (3.67 ml; 0.05 mol) was added a solution of potassium cyanide (3.25 g; 0.05 mol) in water (25 ml) dropwise over 10 min. After stirring at room temperature overnight, the crude reaction mixture was extracted with diethyl ether (2×200 ml) and the combined extracts washed with brine (200 ml), dried (Na2SO4) and evaporated under reduced pressure to afford a pale yellow oil. This was dissolved in DCM and PS-Isocyanate (4.5 g of resin loading 1.53 mmol/g) added. The mixture was stirred for 3 hours, filtered and the filtrate evaporated to afford the title compound as a colourless semi-solid (2.82 g; 37.5%). 1H NMR (CDCl3) δ(inter alia): 1.10 (3H, d), 1.45 (3H, s), 1.55 (3H, s), 1.75-2.00 (4H, m) 2.65 (1H, m) and 3.05-3.20 (2H, m).

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