Reacción #1904

ord-8a08d4d95931403fb13cf9932fe3b98e

Ecuación de reacción

COc1cc(OCc2ccccc2)ccc1C(=O)c1cc(Cl)ccc1N
2-amino-4'-benzyloxy-5-chloro-2'-methoxybenzophenone
[BH4-].[Na+]
sodium borohydride
COc1cc(OCc2ccccc2)ccc1C(O)c1cc(Cl)ccc1N
2-amino-α-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcohol
Rendimiento 94.5%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Concentraciónthe mixture was concentrated in vacuo
  2. 2
    workup.ADDITIONThe residue was diluted with water (200 ml)
  3. 3
    Extracciónextracted with ethyl acetate (300 ml)
  4. 4
    LavadoThe extract was washed with water
  5. 5
    Secadodried over magnesium sulfate
  6. 6
    Concentraciónconcentrated in vacuo
  7. 7
    OtroThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-2:1)

Procedimiento

To a solution of 2-amino-4'-benzyloxy-5-chloro-2'-methoxybenzophenone (10 g) in methanol (100 ml) was added sodium borohydride (1.4 g). After being stirred for 24 h, the mixture was concentrated in vacuo. The residue was diluted with water (200 ml) and extracted with ethyl acetate (300 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=4:1-2:1) to give 2-amino-α-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcohol (9.5 g) as colorless crystals (mp=101°-103° C.).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05726306uspto-grants-1998_03