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

HRID 1809

Reaction equation

HRID 1809 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[CH:4]([OH:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][C:6]=1[O:19][CH3:20].[CH:27](=O)[C:28]([CH3:31])([CH3:30])[CH3:29].C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[CH2:12]([O:11][C:8]1[CH:9]=[CH:10][C:5]([CH:4]([OH:21])[C:3]2[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:2]=2[NH:1][CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:6]([O:19][CH3:20])[CH:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 12417PivalaldehydeHCID 5003444Sodium cyanoborohydrideHCID 539319582-Amino-alpha-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcohol

Product 1

HCID 54116645alpha-(4-Benzyloxy-2-methoxyphenyl)-2-neopentylamino-5-chlorobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  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)

Sources & evidence

ORD record
ord-b478747f94e9498ba6d526c52d811437
Source dataset
uspto-grants-1998_03
Patent number
US05726306

Linked notes

Loading…