Triethylamine → HCID 19801627, compound

Participants

Reaction Steps

A solution of diethylphosphite (1 ml, 6.75 mmol) and triethylamine (5 ml) is stirred under a nitrogen atmosphere and then treated with tetrakis (triphenylphosphine) palladium (0) (0.4 g). A solution of methyl N-[(3-bromophenyl)methyl]glycinate (Example C) (1.62 g, 6.28 mmol) in toluene (10 ml) is degassed in vacuo, added to the palladium catalyst mixture, and the reaction vessel immersed in a 105° C. oil bath for 17 hours. The reaction mixture is cooled to room temperature and diluted with diethyl ether. An insoluble precipitate is removed by filtration and the filtrate evaporated to give a yellow residue. The product is purified by chromatography on silica gel (0-5% methanol in chloroform as eluant). 1H-NMR: 4H, m, 7.9-7.3 ppm; 4H, m, 4.25-3.95; 2H, s, 3.8; 3H, s, 3.7; 2H, s, 3.4; 6H, t, 1.25.

Provenance & Evidence