Реакция #1904

ord-8a08d4d95931403fb13cf9932fe3b98e

Уравнение реакции

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
Выход 94.5%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Концентрированиеthe mixture was concentrated in vacuo
  2. 2
    workup.ADDITIONThe residue was diluted with water (200 ml)
  3. 3
    Экстракцияextracted with ethyl acetate (300 ml)
  4. 4
    ПромывкаThe extract was washed with water
  5. 5
    Сушкаdried over magnesium sulfate
  6. 6
    Концентрированиеconcentrated in vacuo
  7. 7
    ДругоеThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-2:1)

Методика

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.).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05726306uspto-grants-1998_03