Reacción #87264

Ecuación de reacción

N1,N1′-([1,1′-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-aminopropyl)propane-1,3-diamine)

isobutyraldehyde

NaOH

Sodium borohydride

→

desired product

N1,N1′-([1,1′-Biphenyl]-3,5-diylbis(methylene))bis(N3-(3-(isobutylamino)propyl)propane-1,3-diamine)

Disolventes

MeOH

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction mixture was stirred for 1 h
2. 2
   ConcentraciónThe reaction mixture was concentrated under reduced pressure
3. 3
   Otroto afford a white solid
4. 4
   workup.STIRRINGthe mixture was stirred for 1 h
5. 5
   OtroThe layers were separated
6. 6
   Extracciónthe aqueous layer was extracted with EtOAc (200 mL)
7. 7
   SecadoThe combined organics were dried over Na2SO4
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated under reduced pressure

Procedimiento

To a round-bottom flask was added the crude N1,N1′-([1,1′-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-aminopropyl)propane-1,3-diamine) (3.5 g, 8.0 mmol) and MeOH (50 mL). To the solution was added isobutyraldehyde (1.15 g, 15.9 mmol) and the reaction mixture was stirred at rt for 24 h. Sodium borohydride (1.2 g, 31.9 mmol) was added and the reaction mixture was stirred for 1 h. The reaction mixture was concentrated under reduced pressure to afford a white solid. Aq. NaOH (10%, 200 mL) and EtOAc (200 mL) were added, and the mixture was stirred for 1 h. The layers were separated and the aqueous layer was extracted with EtOAc (200 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the desired product as a clear oil which was used without further purification.

Fuente