Morpholine → (+/-)-1-[3-(Benzhydrylidene-amino)-4-cyano-benzyl]-6-oxo-piperazine-2-carboxylic acid methyl ester

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Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (237 mg, 0.2 mmol) is added to a solution containing (±)-4-[3-(benzhydrylidene-amino)-4-cyano-benzyl]-5-oxo-piperazine-1,3-dicarboxylic acid 1-allyl ester 3-methyl ester (1.10 g, 2.05 mmol) and morpholine (894 mg, 10.2 mmol) in CH2Cl2 (30 mL). After ˜5 min, the reaction mixture is absorbed onto silica gel and chromatographed (CH2Cl2 to 10% MeOH/CH2Cl2) to provide 900 mg (97%) of the title compound as a viscous yellow oil. 1H NMR (300 MHz, CDCl3) δ1.83 (br s, 1H), 2.95 (dd, J=13.5, 4.3 Hz, 1H), 3.27 (br d, J=13.5 Hz, 1H), 3.46-3.72 (m, 4H), 3.73 (s, 3H), 5.40 (d, J=15.3 Hz, 1H), 6.57 (br s, 1H), 6.83 (dd, J=8.0, 1.2 Hz, 1H), 7.17-7.50 (m, 9H), 7.75-7.77 (m, 2H) ppm; MS (ion spray): m/z 453 (M+H).

Provenance & Evidence