HCID 67206109, compound → HCID 58288401, compound

Participants

Reaction Steps

7.70 g (30.3 mmol) of the mixture of methyl 3-(3-amino-4-chlorophenyl)hex-2-enoate and methyl 3-(3-amino-4-chlorophenyl)hex-3-enoate (about 1.5:1, Example 164A) were dissolved in 45 ml of ethyl acetate, 646 mg (0.303 mmol) of palladium on carbon (5%) were added and the mixture was stirred under an atmosphere of hydrogen at atmospheric pressure and RT. After 10 h, the reaction mixture was filtered off through celite, the residue was washed with ethyl acetate and the filtrate was concentrated. The residue was taken up in about 50 ml of ethyl acetate, another about 650 mg of palladium on carbon (5%) were added and the mixture was stirred under an atmosphere of hydrogen at atmospheric pressure and RT. After a further 36 h, the reaction mixture was once more filtered off through celite, the residue was washed with ethyl acetate and the filtrate was concentrated. The residue was taken up in 800 ml of ethyl acetate, once more about 650 mg of palladium on carbon (5%) were added and the mixture was stirred under an atmosphere of hydrogen at atmospheric pressure and RT for 24 h. Again, the reaction mixture was filtered off through celite, the residue was washed with ethyl acetate and the filtrate was concentrated. The residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1 to 10:1). This gave a total of 4.79 g of a mixture of target product and starting material. This mixture was dissolved in 180 ml of ethyl acetate, another 603 mg (0.566 mmol) of palladium on carbon (10%) were added and the mixture was stirred under an atmosphere of hydrogen at atmospheric pressure and RT overnight. The reaction mixture was filtered off through celite, the residue was washed with ethyl acetate, the filtrate was concentrated and the residue was dried under high vacuum. This gave 4.45 g (about 57% of theory) of the target product.

Provenance & Evidence