Red-Al → rac-(1R*,2R*,4R*)-2-{2-[methyl-(3-methylamino-propyl)-amino]-ethyl}-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a cold solution of 88 mg of rac-(2-{[2-((1R*,2R*,4R*)-2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl]-methyl-carbamoyl}-ethyl)-carbamic acid tert.-butyl ester in 5 mL THF was added dropwise 0.5 mL Red-Al, 65% toluenel. The ice bath was removed and the reaction mixture was heated to 60° C. for 1.5 h. The reaction was cooled with an ice bath and quenched by careful addition of 1M NaOH. After stirring for 10 min, the 2 phases were separated and the organic phase was concentrated in vacuo to obtain 80 mg of crude rac-(1R*,2R*,4R*)-2-{2-[methyl-(3-methylamino-propyl)-amino]-ethyl}-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol as yellow oil.

Herkunft & Nachweise