Triethylamine → HCID 86680654, compound

Participants

Reaction Conditions

Reaction Steps

Carbon monoxide gas was bubbled through a reaction mixture containing Et3N (4.742 g, 6.532 ml, 48.86 mmol), tert-butyl (3R)-3-(4-iodophenyl)morpholine-4-carboxylate 8 (5.21 g, 13.39 mmol) and Pd(dppf)Cl2—CH2Cl2 (1.093 g, 1.339 mmol) in methanol (157 mL) cooled in an ice bath for 10 mins. The reaction vessel was quickly sealed and the reaction mixture heated at 65° C. for 18 h. The reaction mixture cooled to rt and filtered through celite, washing through with methanol. The filtrate was concentrated in vacuo and crude product purified by ISCO companion (330 g SiO2 0 to 20% EtOAc/petroleum ether) and the product fractions combined and concentrated in vacuo to leave the product as a colourless oil (6.91 g, 81% yield); 1H NMR (400.0 MHz, DMSO) d 1.39 (9H, s), 3.01 (1H, m), 3.51 (1H, m), 3.71-3.85 (6H, m), 4.29 (1H, m), 5.04 (1H, s), 7.48 (2H, m) and 7.97 (2H, m) ppm.

Provenance & Evidence