Water → 1-(1,1-Dimethylethyl) (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate

Participants

Reaction Steps

Sodium azide (206 mg) was added to a stirred solution of N-tert-butoxycarbonyl-cis-4-p-toluenesulfonyloxy-L-proline 3-quinolylamide (C, 805 mg) in N,N-dimethylformamide (8 mL)-water (1.5 mL). After sting at 70° C. for 4 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 (chloroform:ethyl acetate=1:1 to 1:2, v/v) to afford the title compound (532 mg) as a pale yellow sticky oil: 1H NMR (400 MHz, CD3OD) δ 1.3-1.5 (m, 9H), 2.32 (m, 1H), 2.47 (m, 1H), 3.63 (m, 1H), 3.72 (m, 1H), 4.38 (m, 1H), 4.48 (m, 1H), 7.60 (m, 1H), 7.69 (m, 1H), 7.90 (m, 1H), 7.98 (m, 1H), 8.72-8.75 (m, 1H), and 8.92-8.93 (m, 1H).

Provenance & Evidence