Chlorosuccinimide → HCID 141627790, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (3R)-3-[4-[hydroxyiminomethyl]phenyl]morpholine-4-carboxylate 12 (5.57 g, 18.18 mmol) in DMF (33.06 mL) at 55° C. was added 1-chloropyrrolidine-2,5-dione (2.549 g, 19.09 mmol) and the resulting mixture heated at 55° C. for 20 mins. The reaction mixture was then cooled to rt and diluted with EtOAc (50 mL) and water (50 mL) and the organic layer separated. The aqueous later was extracted further with extracted with EtOAc (2×50 mL) and the combined organic extracts were washed with water (3×50 mL) and brine (1×50 mL), dried over MgSO4, filtered and concentrated in vacuo to leave the product as a white foam (5.78 g, 89% yield); 1H NMR (400.0 MHz, DMSO) d 1.23 (9H, s), 3.37 (1H, m), 3.48 (1H, m), 3.75 (3H, m), 4.26 (1H, m), 5.01 (1H, s), 7.43 (2H, m), 7.78 (2H, m) and 12.40 (1H, s) ppm

Provenance & Evidence