1-Naphthaldehyde → methyl (2E)-3-(5-{[(3R)-1-(1-naphthylmethyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate

Participants

Reaction Steps

A mixture of 1-naphthaldehyde (143 μl), methyl (2E)-3-{5-[(3R)-3-pyrrolidinylamino]-2-pyrazinyl}acrylate dihydrochloride (260 mg) and DIEA (282 μl) in dichloromethane (20 mL) was stirred at ambient temperature for 1 hour. After then, sodium triacetoxyborohydride (515 mg) was added and stirred overnight. Water and chloroform was added to the reaction mixture, and organic layer was separated. Aqueous layer was extracted twice with chloroform and combined organic layer was washed twice with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography on silica gel to give methyl (2E)-3-(5-{[(3R)-1-(1-naphthylmethyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate (480 mg).

Provenance & Evidence