Dimedone → HCID 118122135, compound

Participants

Reaction Steps

1.30 g (2.56 mmol) of tert-butyl (3S)-3-[3-({(3R)—N-[(allyloxy)carbonyl]-4,4,4-trifluorovalyl}amino)-4-chlorophenyl]butanoate (Example 42A, diastereomer mixture) and 2.88 g (20.5 mmol) of dimedone were initially charged in 8.7 ml of abs. THF. At RT, the solution was deoxygenated by passing through argon for 30 min. Subsequently 59.3 mg (0.051 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 10:1) and separated. This gave 591 mg of the target compound (54.5% of theory).

Provenance & Evidence