Water → 1-tert-Butyl 2-methyl (2S,4R)-4-cyanopyrrolidine-1,2-dicarboxylate

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Reaction Conditions

Reaction Steps

Sodium cyanide (245 mg) was added to a stirred solution of N-tert-butoxycarbonyl-cis-4-p-toluenesulfonyloxy-L-proline methyl ester (Compound D101 (K), 1.00 g) in N,N-dimethylformamide (10 mL)-water (22 mL). After stirring at 65° C. for 16 hr, the solvents were removed in vacuo. The residue was diluted with ethyl acetate, and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate:toluene=1:20, v/v) to give the title compound (197 mg): 1H NMR (400 MHz, CDCl3) δ 1.40 (s, 9H), 2.33-2.52 (m, 2H), 3.25 (m, 1H), 3.69 (m, 1H), 3.75 (s, 3H), 3.90 (m, 1H), and 4.37-4.49 (m, 1H).

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