p-Toluenesulfonic acid → HCID 11453842, compound

Participants

Reaction Steps

To a solution of 80 mg (0.28 mmol) of 3-(4-chlorophenyl)-2(S)(3-cyanophenyl)-1(S)-methyl-propylamine in 1.5 mL of toluene, 60 mg of 1-phenyl-2(1H-pyrazol-1-yl)ethanone and 5 mg of TsOH were added. Powdered 4A molecular sieves (˜300 mg) were added to the reaction and it was heated to reflux for 5 hr. The mixture was allowed to cool overnight, filtered and the solid washed with EtOAc. The filtrate was concentrated and the residue was dissolved in 1.5 mL of THF, 0.1 mL of acetic acid. This solution was treated with 20 mg of NaCNBH3 for 1.5 hr. The reaction was diluted with EtOAc, washed with saturated NaHCO3, brine, dried and concentrated. The residue was purified on a prep TLC plate using 50% EtOAC-hexane as eluant to isolate of the higher Rf isomer, 3-(1(S)-(4-chlorobenzyl)-2(S)-((1-phenyl-2-(1H-pyrazol-1-yl)ethyl)amino)propyl)benzonitrile (Diastereomer A) LC-MS: m/e=455 (M+1), 457 (M+3) (3.16 min). and the lower Rf isomer, 3-(1(S)-(4-chlorobenzyl)-2(S)-(1-phenyl-2-(1H-pyrazol-1-yl)ethyl)amino)propyl)benzonitrile (Diastereomer B) LC-MS: m/e=455 (M+1), 457 (M+3) (3.12 min).

Provenance & Evidence