Dimedone → HCID 126504116, compound

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Reaction Steps

1.39 g (2.74 mmol) of tert-butyl (3S)-3-[3-({N-[(allyloxy)carbonyl]-4,4,4-trifluorovalyl}amino)-4-chlorophenyl]butanoate (Example 41A, mixture of 4 isomers) and 3.08 g (21.9 mmol) of dimedone were initially charged in 9.4 ml of abs. THF. At RT, the solution was deoxygenated by passing through argon for 30 min Subsequently 63.4 mg (0.055 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 950 mg of the target compound as diastereomer mixture 1 (81.9% of theory).

Provenance & Evidence