Acetic Acid → 5-Chloro-alpha-(2,4,6-trimethoxyphenyl)-2-(neopentylamino)benzyl alcohol

HRID 1419046Notes

Reaction equation

HRID 1419046 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:3]=1[CH:4]([OH:17])[C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([O:13][CH3:14])=[CH:7][C:6]=1[O:15][CH3:16].[CH3:23][C:24]([CH3:28])([CH3:27])[CH:25]=O.C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[Cl:22][C:19]1[CH:20]=[CH:21][C:2]([NH:1][CH2:23][C:24]([CH3:28])([CH3:27])[CH3:25])=[C:3]([CH:18]=1)[CH:4]([OH:17])[C:5]1[C:6]([O:15][CH3:16])=[CH:7][C:8]([O:13][CH3:14])=[CH:9][C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 12417PivalaldehydeHCID 5003444Sodium cyanoborohydrideHCID 544145002-Amino-5-chloro-alpha-(2,4,6-trimethoxyphenyl)benzyl alcohol

Product 1

HCID 541447755-Chloro-alpha-(2,4,6-trimethoxyphenyl)-2-(neopentylamino)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After a solution of 2.5 g of 2-amino-5-chloro-α-(2,4,6-trimethoxyphenyl)benzyl alcohol, 1.01 ml of trimethylacetaldehyde and 0.56 g of acetic acid in 30 ml of ethanol was stirred at room temperature for 1.5 hours, 0.81 g of sodium cyanoborohydride was added, followed by stirring overnight. After concentration and subsequent dilution with water, the solution was extracted with ethyl acetate. After solvent removal, the residue was subjected to silica gel column chromatography to yield 2.2 g of a crystal.

Workup

  1. concentrationAfter concentration and subsequent dilution with water
  2. extractionthe solution was extracted with ethyl acetate
  3. customAfter solvent removal

Sources & evidence

ORD record
ord-f77a488296fb43c2854d504fe49283e9
Source dataset
uspto-grants-1999_03
Patent number
US05885979

Reaction notes

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