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

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).

1. additionsubstrate were added
2. stirringby stirring at room temperature for 14 hours
3. customAfter completion of the reaction
4. customthe solvent was removed by evaporation
5. customthe residue was purified by silica gel column chromatography

ORD record

ord-908a04923063430dae1cd9244c0a371f

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06888012B2