Reaction #1904

Reaction equation

2-amino-4'-benzyloxy-5-chloro-2'-methoxybenzophenone

sodium borohydride

→

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

Yield 94.5%

Solvents

methanol

Conditions

Workup

1. 1
   Concentrationthe mixture was concentrated in vacuo
2. 2
   workup.ADDITIONThe residue was diluted with water (200 ml)
3. 3
   Extractionextracted with ethyl acetate (300 ml)
4. 4
   WashThe extract was washed with water
5. 5
   Dryingdried over magnesium sulfate
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-2:1)

Procedure

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.).

Source