Réaction #220660

Équation de réaction

3-(1(S)-(4-chlorobenzyl)-2(S)-((1-(3-bromophenyl)-2-cyanoethyl)amino)propyl)benzonitrile

DMF

→

3-(1(S)-(4-chlorobenzyl)-2(S)-((1-(3-cyanophenyl)-2-cyanoethyl)amino)propyl)benzonitrile

Solvants

water

Conditions de réaction

Traitement

1. 1
   AutreThe solution was degassed
2. 2
   Autreby bubbling N2 for 30 min
3. 3
   AutreThe vial was sealed
4. 4
   TempératureAfter the reaction cooled
5. 5
   Filtrationit was filtered through a pad of CELITE, diatomaceous earth
6. 6
   Lavagethe solids were washed with ether
7. 7
   workup.ADDITIONThe filtrate was diluted with ether
8. 8
   Lavagewashed with water, and brine
9. 9
   Autredried
10. 10
    Concentrationconcentrated
11. 11
    AutreThe residue was purified by prep TLC

Mode opératoire

A solution of 164 mg (0.33 mmol) of 3-(1(S)-(4-chlorobenzyl)-2(S)-((1-(3-bromophenyl)-2-cyanoethyl)amino)propyl)benzonitrile (mixture of two diastereomers) in 2 mL of DMF and 0.02 mL of water was treated with 35 mg of Zinc cyanide, 7 mg (0.008 mmol) of tris(dibenzylidineacetone) dipalladium and 11 mg (0.02 mmol) of 1,1′-bis(diphenylphosphino)ferrocene. The solution was degassed by bubbling N2 for 30 min, while the color changed from brown to yellow-orange. The vial was sealed and heated in a microwave reactor at 180° C. for 1 hr. After the reaction cooled, it was filtered through a pad of CELITE, diatomaceous earth, and the solids were washed with ether. The filtrate was diluted with ether, washed with water, and brine, then dried and concentrated. The residue was purified by prep TLC to obtain the less polar isomer, 3-(1(S)-(4-chlorobenzyl)-2(S)-((1-(3-cyanophenyl)-2-cyanoethyl)amino)propyl)benzonitrile (Diastereomer A); LC-MS: m/e=439 (M+1), 441 (M+3) (3.62 min) and more polar isomer 3-(1(S)-(4-Chlorobenzyl)-2(S)-((1-(3-cyanophenyl)-2-cyanoethyl)amino)propyl)benzonitrile (Diastereomer B); LC-MS: m/e=439 (M+1), 441 (M+3) (3.41 min).

Source