Pyridine → cis-(1R,2S)-2-(3-aminopropyl)-1-[1-(4-chlorophenyl)imidazol-4-yl]cyclopropane-1-carboxylic acid

Participants

Reaction Steps

The compound (180 mg) obtained in Reference Example 16 was dissolved in methylene chloride (5 mL). To the solution, copper (II) acetate (76 mg), pyridine (67 μL), molecular sieve 4A (36 mg), and 4-chlorophenylboronic acid (129 mg) were added, and the mixture was stirred overnight at room temperature under an oxygen atmosphere. The progress of the reaction was checked by TLC. Then, a saturated aqueous solution of sodium bicarbonate (10 mL) and disodium ethylenediaminetetraacetate dihydrate (184 mg, 0.49 mmol) were added thereto, and the mixture was stirred for a while. The reaction solution was filtered using a syringe with a filter (Biotage, ISOLUTE Phase Separator) containing an appropriate amount of celite. The filtrate was further washed with methylene chloride. The collected organic layers were combined, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent: methylene chloride→methylene chloride/ethyl acetate=80/20) to obtain the title compound (190 mg).

Provenance & Evidence