Methylamine → rac-(1R*,2R*,4R*)-2-(2-methylamino-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol

Participants

Reaction Conditions

Reaction Steps

4.28 g of rac-toluene-4-sulfonic acid (1R*,2R*,4R*)-2-(2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl ester (see Example 1, procedures P1.1 and P1.2) were dissolved in a 8 M solution of MeNH2 in EtOH (54 mL). The mixture was stirred overnight at 40° C., diluted with DCM and washed with sat.-NaHCO3. The organic phase was dried over anh. Na2SO4 and concentrated to give 2.73 g of rac-(1R*,2R*,4R*)-2-(2-methylamino-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol as a white solid.

Provenance & Evidence