N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamide → 2-Chloro-1-[3-(dimethylamino)phenyl]ethan-1-ol

Participants

Reaction Steps

A solution of di-μ-chlorodichlorobis(pentamethylcyclopentadienyl)dirhodium (III) (1.5 mg, 0.0025 mmol) and (1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (3.7 mg, 0.01 mmol) in isopropyl alcohol (4.75 ml) was heated at 80° C. for 20 minutes while stirring. After cooling the solution to room temperature, a 0.1 M potassium tert-butoxide isopropyl alcohol solution (0.25 ml, 0.025 mmol) and 2-chloro-3′-(dimethylamino)acetophenone (98.8 mg, 0.5 mmol) as a reaction substrate were added thereto, followed by stirring at room temperature for 14 hours. After completion of the reaction, the solvent was removed by evaporation, and the residue was purified by silica gel column chromatography to give a desired compound, (+)-2-chloro-1-(3′-dimethylaminophenyl)ethanol (95.3 mg; yield: 95.3%; optical purity: 98.8% ee).

Provenance & Evidence