Dimedone → HCID 90014535, compound

Participants

Reaction Steps

1.40 g (2.92 mmol) of ethyl (2R)-3-[3-({N-[(allyloxy)carbonyl]-4,4,4-trifluorovalyl}amino)-4-chlorophenyl]-2-methylpropanoate (Example 38A, mixture of 4 isomers) and 3.28 g (23.4 mmol) of dimedone were initially charged in 10 ml of abs. THF. At RT, the solution was deoxygenated by passing through argon for 30 min. Subsequently 67.6 mg (0.058 mmol) of tetrakis(triphenylphosphine)palladium(0) were added and the mixture was stirred at RT overnight. After dilution with ethyl acetate, the mixture was washed twice with sat. sodium bicarbonate solution and once with sat. sodium chloride solution. The organic phase was dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 40:1→20:1) and separated. This gave 844 mg of the target compound as diastereomer mixture 1 (73.1% of theory).

Provenance & Evidence