Diisopropylethylamine → rac-N-(3-{[2-((1R*,2R*,4R*)-2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl]-methyl-amino}-propyl)-3-methoxy-2-methoxymethyl-2,N-dimethyl-propionamide

Beteiligte Stoffe

Reaktionsschritte

To a solution of 65 mg 3-methoxy-2-methoxymethyl-2-methyl-propionic acid in 0.5 mL DCM was added 0.14 mL DIPEA followed by 133 mg HATU. The resulting mixture was stirred at rt for 20 min before 88 mg of rac-(1R*,2R*,4R*)-2-{2-[methyl-(3-methylamino-propyl)-amino]-ethyl}-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol, dissolved in 1 mL DCM was added. After stirring overnight the reaction was quenched with water. The water phase was extracted with DCM, the combined organic phases were washed with brine, dried and concentrated in vacuo. The residue was purified by CC with EtOAc-MeOH (3:1) to obtain 115 mg of rac-N-(3-{[2-((1R*,2R*,4R*)-2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl]-methyl-amino}-propyl)-3-methoxy-2-methoxymethyl-2,N-dimethyl-propionamide as colorless oil.

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