Reaction #1905

Reaction equation

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

Solvents

ethanol

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred for 24 h
2. 2
   ConcentrationAfter the mixture was concentrated in vacuo
3. 3
   workup.ADDITIONthe residue was diluted with water (200 ml)
4. 4
   Extractionextracted with ethyl acetate (200 ml)
5. 5
   WashThe extract was washed with water
6. 6
   Dryingdried over magnesium sulfate
7. 7
   Concentrationconcentrated in vacuo
8. 8
   OtherThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Procedure

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.

Source