Sodium cyanoborohydride → 3-{4-[(4-Cyclohex-1-enylphenylamino)methyl]benzoylamino}propionic acid methyl ester

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Reaction Steps

3-(4-Formylbenzoylamino)propionic acid methyl ester (10 g, 42.5 mmol) was dissolved in methanol (100 ml). With mechanical stirring a solution of 4-cyclohex-1-enylaniline (7.4 g, 42.5 mmol) in methanol (15 ml) was added and the resulting suspension was stirred at room temperature for 2.5 hours. Sodium cyano borohydride (4.01 g, 63.8 mmol) was added in portions and the resulting mixture was stirred at room temperature for 4 days. Filtration afforded 7.1 g of a solid and recrystallisation from methanol afforded 3.55 g of 3-{4-[(4-cyclohex-1-enylphenylamino)methyl]benzoylamino}propionic acid methyl ester.

Provenance & Evidence