Nitrogen → HCID 131722858, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl (R)4-brom-2-(1-phenylethoxy)-phenylacetate (0.50 g, 1.43 mmol) and diethylcrotonamide (0.30 g, 2.1 mmol) in triethylamine (5 mL) is deoxygenated with bubbling N2 for 10 minutes in a small pressure tube. Palladium (II) acetate (16 mg, 0.07 mmol) and tris-(o-tolyl)-phosphine (44 mg, 0.14 mmol) is then added. The tube is then sealed, and the mixture heated to 100° C. for 2.5 hours. After cooling, the mixture (now dark, with precipitate present) is diluted with ethyl acetate (20 mL), and the mixture is filtered through celite, and the filtrate evaporated and chromatographed (silica, 30% ethyl acetate/hexane) to yield methyl (E)-(R)-(−)-[5-(2-diethylcarbamoyl-1-methylvinyl)-2-(1-phenylethoxy)-phenyl]-acetate as a yellow oil.

Provenance & Evidence