Acetic Acid → alpha-(4-Benzyloxy-2-methoxyphenyl)-2-neopentylamino-5-chlorobenzyl alcohol

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.

1. stirringthe mixture was stirred for 24 h
2. concentrationAfter the mixture was concentrated in vacuo
3. additionthe residue was diluted with water (200 ml)
4. extractionextracted with ethyl acetate (200 ml)
5. washThe extract was washed with water
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated in vacuo
8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

ORD record

ord-b478747f94e9498ba6d526c52d811437

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05726306