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

HRID 1791

Reaction equation

HRID 1791 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-775bed0ad28c49fbb6c1ce5df50c6d65
Source dataset
uspto-grants-1998_03
Patent number
US05726306

Linked notes

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