2-Hydroxy-2-methyl-1-phenylpropan-1-one → 3-(1(S)-(4-chlorobenzyl)-2(S)-((2-hydroxy-2-methyl-1-phenylpropyl)amino)propyl)benzonitrile

Beteiligte Stoffe

Reaktionsschritte

To a solution of 250 mg (0.877 mmol) of 3-(4-chlorophenyl)-2(S)(3-cyanophenyl)-1(S)-methyl-propylamine in 3 mL of dichloroethane, 134 μL (0.88 mmol) of 2-hydroxy-2-methylpropiophenone and 280 mg (1.32 mmol) of sodium triacetoxyborohydride were added. After stirring for 3 hr, the reaction was quenched with water and the organic layer was removed with a pipet. This layer was purified by prep TLC using 50% EtOAc/hexane as an eluant to isolate 3-(1(S)-(4-chlorobenzyl)-2(S)-((2-hydroxy-2-methyl-1-phenylpropyl)amino)propyl)benzonitrile (diastereomer A) as a higher Rf isomer (LC-MS: m/e=433 (M+1), 3.09 min) and 3-(1(S)-(4-Chlorobenzyl)-2(S)-((2-hydroxy-2-methyl-1-phenylpropyl)amino)propyl)benzonitrile (diastereomer B) as a lower Rf isomer. LC-MS: m/e=433 (M+1), 3.09 min.

Herkunft & Nachweise