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

HRID 1791

Reaktionsgleichung

Reaktionsgleichung von HRID 1791
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-775bed0ad28c49fbb6c1ce5df50c6d65
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726306

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