p-Toluenesulfonic acid → HCID 60151763, compound

Participants

Reaction Steps

Add TsOH (5.0 g, 29.1 mmol) to a solution of 2-dimethylaminomethyl-3-(3-hydroxy-phenyl)-bicyclo[3.2.1]octan-3-ol (4.8 g, 17.5 mmol) in toluene (150 mL). Heat the reaction mixture to reflux for 2 hours and then quench the reaction by addition of saturated aqueous K2CO3 (20 mL). Extract the aqueous layer with EtOAc (60 mL×3). The combined organic layers are washed with brine, dried over Na2SO4 and evaporated under vacuum. Purify the residue by preparative HPLC to yield 3-(4-dimethylaminomethyl-bicyclo[3.2.1]oct-2-en-3-yl)-phenol (2.27 g, 50.2%; MS (m/z): 258 (M+1)) and 3-(2-((dimethylamino)methyl)bicyclo[3.2.1]oct-2-en-3-yl)phenol (517 mg, 11.5%; MS (m/z): 258 (M+1)) as white solid. Two isomers show comparable biological activity in bioassay.

Provenance & Evidence