Reacción #1905

Ecuación de reacción

sodium cyanoborohydride

2-amino-α-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcohol

pivalaldehyde

acetic acid

→

α-(4-benzyloxy-2-methoxyphenyl)-2-neopentylamino-5-chlorobenzyl alcohol

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred for 24 h
2. 2
   ConcentraciónAfter the mixture was concentrated in vacuo
3. 3
   workup.ADDITIONthe residue was diluted with water (200 ml)
4. 4
   Extracciónextracted with ethyl acetate (200 ml)
5. 5
   LavadoThe extract was washed with water
6. 6
   Secadodried over magnesium sulfate
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   OtroThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Procedimiento

A mixture of 2-amino-α-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcohol (9.5 g), pivalaldehyde (3.35 ml), acetic acid (1.85 g) and ethanol (200 ml) was stirred for 30 min. To the mixture was added sodium cyanoborohydride (2.33 g) and the mixture was stirred for 24 h. After the mixture was concentrated in vacuo, the residue was diluted with water (200 ml) and extracted with ethyl acetate (200 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give α-(4-benzyloxy-2-methoxyphenyl)-2-neopentylamino-5-chlorobenzyl alcohol (10.0 g) as a colorless oil.

Fuente