Reacción #363060

Ecuación de reacción

2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

3,4-dibenzyloxybenzaldehyde

acetic acid

cyano sodium borohydride

→

2-(3,4-dibenzyloxybenzyl)amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

Rendimiento 75.5%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture was concentrated, to which
2. 2
   workup.ADDITIONwere added water (50 ml) and ethyl acetate (80 ml)
3. 3
   Extracciónfollowed by extraction
4. 4
   LavadoThe organic layer was washed with water
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off

Procedimiento

In methanol (20 ml) were dissolved 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.6 g) and 3,4-dibenzyloxybenzaldehyde (0.55 g). To the solution were added acetic acid (0.12 g) and cyano sodium borohydride (0.13 g). The mixture was stirred for 1.5 hour at 60° C. The reaction mixture was concentrated, to which were added water (50 ml) and ethyl acetate (80 ml), followed by extraction. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to leave 2-(3,4-dibenzyloxybenzyl)amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.83 g) as colorless crystals, m.p.: 118-120° C.

Fuente