Potassium Phosphate, Tribasic → tert-Butyl 1-(3-amino-4-cyclopropylbenzyl)cyclopropanecarboxylate

Participants

Reaction Conditions

Reaction Steps

200 mg (0.71 mmol) of tert-butyl 1-(3-amino-4-chlorobenzyl)cyclopropanecarboxylate were dissolved in 6 ml of dioxane, the mixture was inertized with argon and 122 mg (1.42 mmol) of cyclopropylboronic acid, 256 mg (1.21 mmol) of potassium phosphate, 5 mg (0.02 mmol) of tricyclohexylphosphine and 6.5 mg (0.007 mmol) of tris(dibenzylideneacetone)dipalladium were added. The reaction mixture was then stirred in a microwave apparatus (Biotage) at a target temperature of 150° C. for 1 h. The reaction was checked by TLC (mobile phase cyclohexane/ethyl acetate 4:1), after which a further 10 mg of tricyclohexylphosphine and 13 mg of tris(dibenzylideneacetone)dipalladium were metered in, and the reaction mixture was stirred at 150° C. for another 2 h. The mixture was then filtered through kieselguhr, the residue was washed with dioxane and the combined filtrate was concentrated to dryness. The residue obtained was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1). This gave 120 mg (59% of theory) of the target compound.

Provenance & Evidence