Triethylamine → 2-((E)-2-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-vinyl)-piperidine-1-carboxylic Acid Tert-butyl Ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (120 mg, 0.22 mmol) in MeCN (2 mL) is added 2-vinylpiperidine-1-carboxylic acid tert-butyl ester (51 mg, 0.242 mmol), triethylamine (33 mg, 0.33 mmol), 2,2′-bis(di-t-butylphosphino)biphenyl (2.6 mg) and Pd(OAc)2 (1.0 mg). The vessel is flushed with nitrogen and the mixture is stirred at 100° C. for 4 h. The mixture is partitioned between EtOAc/water and the organic phase is washed with water, brine and dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using a gradient of EtOAc/hexane (5 to 25%) as eluent to give the title compound.

Provenance & Evidence